Substituted pyridines having a herbicidal effect

ABSTRACT

Substituted pyridines of the formula I 
                         
in which the variables are defined according to the description, their agriculturally suitable salts, processes and intermediates for preparing the pyridines of the formula I, compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one pyridine compound of the formula I to act on plants, their seed and/or their habitat.

This application is a National Stage application of InternationalApplication No. PCT/EP2009/063387, filed Oct. 14, 2009, the entirecontents of which is hereby incorporated herein by reference. Thisapplication also claims priority under 35 U.S.C. §119 to European PatentApplication No. 08167850.0 filed Oct. 29, 2008, the entire contents ofwhich is hereby incorporated herein by reference.

The present invention relates substituted pyridines of the formula I

in which the variables have the following meaning:

-   R¹ is O—R^(A), S(O)_(n)—R^(A) or O—S(O)_(n)—R^(A);    -   R^(A) is hydrogen, C₁-C₄-alkyl, Z—C₃-C₆-cycloalkyl,        C₁-C₄-haloalkyl, C₂-C₆-alkenyl, Z—C₃-C₆-cycloalkenyl,        C₂-C₆-alkynyl, Z-(tri-C₁-C₄-alkyl)silyl, Z—C(═O)—R^(a),        NR^(i)R^(ii), Z—P(═O)(R^(a))₂, NR^(i)R^(ii), a 3- to 7-membered        monocyclic or 9- or 10-membered bicyclic saturated, unsaturated        or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms        selected from the group consisting of O, N and S, which may be        partially or fully substituted by groups R^(a) and/or R^(b),        -   R^(a) is hydrogen, OH, C₁-C₈-alkyl, C₁-C₄-haloalkyl,            Z—C₃-C₆-cycloalkyl, C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl,            C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy,            Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy, NR^(i)R^(ii),            C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl,            Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or            9- or 10-membered bicyclic heterocycle which contains 1, 2,            3 or 4 heteroatoms selected from the group consisting of O,            N and S, where the cyclic groups are unsubstituted or            substituted by 1, 2, 3 or 4 groups R^(b);            -   R^(i)R^(ii) independently of one another are hydrogen,                C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₃-C₈-alkenyl,                C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy,                Z—C₁-C₈-haloalkoxy, Z—C(═O)—R^(a), Z-phenyl, a 3- to                7-membered monocyclic or 9- or 10-membered bicyclic                saturated, unsaturated or aromatic heterocycle which                contains 1, 2, 3 or 4 heteroatoms selected from the                group consisting of O, N and S and which is attached via                Z;            -   R^(i) and R^(ii) together with the nitrogen atom to                which they are attached may also form a 5- or 6-membered                monocyclic or 9- or 10-membered bicyclic heterocycle                which contains 1, 2, 3 or 4 heteroatoms selected from                the group consisting of O, N and S;        -   Z is a covalent bond or C₁-C₄-alkylene;    -   n is 0, 1 or 2;-   R² is phenyl, naphthyl or a 5- or 6-membered monocyclic or 9- or    10-membered bicyclic aromatic heterocycle which contains 1, 2, 3 or    4 heteroatoms selected from the group consisting of O, N and S,    where the cyclic groups are unsubstituted or substituted by 1, 2, 3    or 4 groups R^(b);    -   R^(b) independently of one another are Z—CN, Z—OH, Z—NO₂,        Z-halogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₂-C₈-alkenyl,        C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy,        Z—C₃-C₁₀-cycloalkyl, O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a),        NR^(i)R^(ii), Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl and        S(O)_(n)R^(bb),        -   where R^(bb) is C₁-C₈-alkyl or C₁-C₆-haloalkyl and        -   n is 0, 1 or 2;        -   R^(b) together with the group R^(b) attached to the adjacent            carbon atom may also form a five- or six-membered saturated            or partially or fully unsaturated ring which, in addition to            carbon atoms, may contain 1, 2 or 3 heteroatoms selected            from the group consisting of O, N and S;-   X is O, S or N—R³;    -   R³ is hydrogen, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,        C₃-C₆-alkynyl, Z—C₃-C₁₀-cycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,        C₁-C₆-cyanoalkyl, Z-phenyl, Z—C(═O)—R^(a2) or        tri-C₁-C₄-alkylsilyl;        -   R^(a2) is C₁-C₆-alkyl, C₁-C₄-haloalkyl, Z—C₁-C₆-alkoxy,            Z—C₁-C₄-halo-alkoxy or NR^(i)R^(ii);-   Y is O or S;-   A, E, G, M are N or C—R^(c), one of these groups being N;    -   R^(c) is hydrogen or one of the groups mentioned for R^(b);        where in the groups R^(A), R³ and their subsubtituents, the        carbon chains and/or the cyclic groups may be partially or fully        substituted by groups R^(b), or a N-oxide or an agriculturally        suitable salt thereof.

Moreover, the invention relates to processes and intermediates forpreparing the pyridines of the formula I and the N-oxides thereof, theagriculturally usable salts thereof, and also to active compoundcombinations comprising them, to compositions comprising them and totheir use as herbicides, i.e. for controlling harmful plants, and alsoto a method for controlling unwanted vegetation which comprises allowinga herbicidally effective amount of at least one pyridine compound of theformula I or of an agriculturally suitable salt of I to act on plants,their seed and/or their habitat.

Further embodiments of the present invention can be found in the claims,the description and the examples. It is to be understood that thefeatures mentioned above and those still to be illustrated below of thesubject matter of the invention can be applied not only in therespective given combination but also in other combinations withoutleaving the scope of the invention.

WO 2008/009908 and WO 2008/071918 describe herbicidal pyridopyrazines;however, their herbicidal action at low application rates and/or theircompatibility with crop plants leave scope for improvement.

It is an object of the present invention to provide compounds havingherbicidal action. To be provided are in particular active compoundshaving strong herbicidal action, in particular even at low applicationrates, whose compatibility with crop plants is sufficient for commercialapplication.

These and further objects are achieved by the compounds of the formula Idefined at the outset and by their N-oxides and also theiragriculturally suitable salts.

The compounds according to the invention can be prepared analogously tothe synthesis routes described in WO 2008/009908 and WO 2008/071918according to standard processes of organic chemistry, for exampleaccording to the following synthesis route:

Pyridine carboxylic acids of the formula II can be reacted with carbonylcompounds of the formula III to give compounds of the formula IV. In theformulae II and III, the variables have the meaning given for formula I.The group Hal is a halogen atom or another suitable nucleophilic leavinggroup, such as alkoxy or phenoxy.

This reaction is usually carried out at temperatures of from −78° C. to120° C., preferably from −20° C. to 50° C., in an inert organic solventin the presence of a base, such as, for example, triethylamine (cf. J.Agric. and Food Chem. 1994, 42(4), 1019-1025), a catalyst, such as, forexample, dicyclohexylcarbodiimide (cf. Egyptian Journal of Chemistry1994, 37(3), 273-282) or other known coupling agents.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene,o-, m- and p-xylene, halogenated hydrocarbons, such as methylenechloride, chloroform and chlorobenzene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles, such as acetonitrile and propionitrile,ketones, such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamideand dimethylacetamide, particularly preferably halogenated hydrocarbons,such as methylene chloride, chloroform and chlorobenzene. It is alsopossible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal amides, such as lithium amide,sodium amide and potassium amide, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, organometallic compounds, in particular alkali metalalkyls, such as methyllithium, butyllithium and phenyllithium,alkylmagnesium halides, such as methylmagnesium chloride, and alsoalkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxideand dimethoxymagnesium, moreover organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, tributylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to tertiary aminessuch as trimethylamine, triethylamine, tributylamine,diisopropylethylamine. The bases are generally employed in catalyticamounts; however, they can also be used in equimolar amounts, in excessor, if appropriate, as solvents.

The starting materials are generally reacted with one another inequimolar amounts.

The compounds of the formula IV are activated by introducing a leavinggroup L¹. Suitable leaving groups L¹ are, in general, groups whichincrease the electrophilicity of the carbonyl group, for exampleO-alkyl, O-aryl, halides, activated esters or aldehydes (such as, forexample, Weinreb amide), in particular pentafluorophenoxy.

This reaction is usually carried out at temperatures of from −78° C. to120° C., preferably from −20° C. to 50° C., in an inert organic solventin the presence of a base, such as, for example, triethylamine (cf. J.Agric. and Food Chem. 1994, 42(4), 1019-1025), a catalyst, such as, forexample, dicyclohexylcarbodiimide (cf. Egyptian Journal of Chemistry1994, 37(3), 273-282) or other known coupling agents.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene,o-, m- and p-xylene, halogenated hydrocarbons, such as methylenechloride, chloroform and chlorobenzene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles, such as acetonitrile and propionitrile,ketones, such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamideand dimethylacetamide, particularly preferably methylene chloride andtoluene. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal amides, such as lithium amide,sodium amide and potassium amide, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, organometallic compounds, in particular alkali metalalkyls, such as methyllithium, butyllithium and phenyllithium,alkylmagnesium halides, such as methylmagnesium chloride, and alsoalkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxideand dimethoxymagnesium, moreover organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, tributylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to alkali metal andalkaline earth metal carbonates, such as lithium carbonate, potassiumcarbonate, calcium carbonate, cesium carbonate and rubidium carbonate.The bases are generally employed in catalytic amounts; however, they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The starting materials are generally reacted with one another inequimolar amounts.

Suitable agents H-L¹ are alcohols, optionally subst. phenols,N,O-dialkyl-hydroxylamine, in particular pentafluorophenol orN,O-dimethylhydroxylamine.

The compounds of the formula V are cyclized to give the compounds of theformula I.

This reaction is usually carried out at temperatures of from −78° C. to120° C., preferably from −20° C. to 50° C., in an inert organic solventin the presence of a base or a Lewis acid or a catalyst [cf. Silverman,Richard B. J. Am. Chem. Soc. 1981, 103(13), 3910].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene,o-, m- and p-xylene, halogenated hydrocarbons, such as methylenechloride, chloroform and chloro-benzene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles, such as acetonitrile and propionitrile,ketones, such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamideand dimethylacetamide, particularly preferably acetonitrile anddimethylformamide. It is also possible to use mixtures of the solventsmentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal amides, such as lithium amide,sodium amide and potassium amide, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate, calciumcarbonate, cesium carbonate and rubidium carbonate, and also alkalimetal bicarbonates, such as sodium bicarbonate, organometalliccompounds, in particular alkali metal alkyls, such as methyllithium,butyllithium and phenyllithium, alkylmagnesium halides, such asmethylmagnesium chloride, and also alkali metal and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, moreoverorganic bases, for example tertiary amines, such as trimethylamine,triethylamine, tributylamine, diisopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines, such as collidine,lutidine and 4-dimethylaminopyridine, and also bicyclic amines.Particular preference is given to alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate, calciumcarbonate, cesium carbonate and rubidium carbonate.

The bases are generally employed in catalytic amounts; however, they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The starting materials are generally reacted with one another inequimolar amounts.

Alternatively, the compounds of the formula I can also be obtained via areverse reaction sequence, i.e. the reaction of the compounds of theformula II with compounds H-L¹ gives the activated derivatives of theformula VI.

Per se, this reaction is carried out under the conditions mentioned forthe reaction of the formula IV with H-L¹.

The compounds of the formula VI can then be reacted with compounds IIIto give the derivatives of the formula V.

Per se, this reaction is carried out under the conditions mentioned forthe reaction of the formula II with III.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separating the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of colorless orslightly brownish viscous oils which are purified or freed from volatilecomponents under reduced pressure and at moderately elevatedtemperature.

If the intermediates and end products are obtained as solids, thepurification can also be carried out by recrystallization or digestion.

If individual compounds I cannot be obtained by the routes describedabove, they can be prepared by derivatization of other compounds I.

If the synthesis yields mixtures of isomers, a separation is generallyhowever not necessarily required since in some cases the individualisomers can be interconverted during work-up for use or duringapplication (for example under the action of light, acids or bases).Such conversions may also take place after application, for example inthe case of the treatment of plants in the treated plant or in theharmful plant to be controlled.

The organic moieties mentioned for the substituents of the compoundsaccording to the invention are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,such as alkyl, haloalkyl, alkenyl, alkynyl, and the alkyl moieties andalkenyl moieties in alkoxy, haloalkoxy, alkylamino, dialkylamino,N-alkylsulfonylamino, alkenyloxy, alkynyloxy, alkoxyamino,alkylaminosulfonylamino, dialkylaminosulfonylamino, alkenylamino,alkynylamino, N-(alkenyl)-N-(alkyl)amino, N-(alkynyl)-N-(alkyl)amino,N-(alkoxy)-N-(alkyl)amino, N-(alkenyl)-N-(alkoxy)amino orN-(alkynyl)-N-(alkoxy)amino can be straight-chain or branched.

The prefix C_(n)-C_(m)— indicates the respective number of carbons ofthe hydrocarbon unit. Unless indicated otherwise, halogenatedsubstituents preferably carry one to five identical or different halogenatoms, in particular fluorine atoms or chlorine atoms.

The meaning halogen denotes in each case fluorine, chlorine, bromine oriodine.

Examples of other meanings are:

alkyl and the alkyl moieties for example in alkoxy, alkylamino,dialkylamino, N-alkyl-sulfonylamino, alkylaminosulfonylamino,dialkylaminosulfonylamino, N-(alkenyl)-N-(alkyl)amino,N-(alkynyl)-N-(alkyl)amino, N-(alkoxy)-N-(alkyl)amino: saturatedstraight-chain or branched hydrocarbon radicals having one or morecarbon atoms, for example 1 or 2, 1 to 4 or 1 to 6 carbon atoms, forexample C₁-C₆-alkyl, such as methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethyl-butyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethyl-propyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl. In one embodimentaccording to the invention, alkyl denotes small alkyl groups, such asC₁-C₄-alkyl. In another embodiment according to the invention, alkyldenotes relatively large alkyl groups, such as C₅-C₆-alkyl.

Haloalkyl: an alkyl radical as mentioned above, some or all of whosehydrogen atoms are substituted by halogen atoms, such as fluorine,chlorine, bromine and/or iodine, for example chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoro-methyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoro-ethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl,2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl.

Cycloalkyl and the cycloalkyl moieties for example in cycloalkoxy orcycloalkylcarbonyl: monocyclic saturated hydrocarbon groups having threeor more carbon atoms, for example 3 to 6 carbon ring members, such ascyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkenyl and the alkenyl moieties for example in alkenylamino,alkenyloxy, N-(alkenyl)-N-(alkyl)amino, N-(alkenyl)-N-(alkoxy)amino:monounsaturated straight-chain or branched hydrocarbon radicals havingtwo or more carbon atoms, for example 2 to 4, 2 to 6 or 3 to 6 carbonatoms, and a double bond in any position, for example C₂-C₆-alkenyl,such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl.

Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to6, preferably 5 or 6, carbon ring members, such as cyclopenten-1-yl,cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl.

Alkynyl and the alkynyl moieties for example in alkynyloxy,alkynylamino, N-(alkynyl)-N-(alkyl)amino or N-(alkynyl)-N-(alkoxy)amino:straight-chain or branched hydrocarbon groups having two or more carbonatoms, for example 2 to 4, 2 to 6 or 3 to 6 carbon atoms, and a triplebond in any position, for example C₂-C₆-alkynyl, such as ethynyl,1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl.

Alkoxy: alkyl as defined above which is attached via an oxygen atom, forexample methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy,1-methylpropoxy, 2-methyl-propoxy or 1,1-dimethylethoxy, pentoxy,1-methylbutoxy, 2-methylbutoxy, 3-methyl-butoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethyl-propoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methyl-pentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethyl-butoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy.

3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated,unsaturated or aromatic heterocycle which contains 1, 2, 3, or 4heteroatoms selected from the group consisting of O, N and S and whichcan be attached via C or N. Preferred from among these are 5- or6-membered heterocycles.

Saturated or unsaturated heterocyclic groups which are attached via N,such as: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl,isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl,oxazol-5-yl, thiazol-2-yl, thiazol-4-yl and thiazol-5-yl.

Heteroaromatic groups which are attached via C, such as: pyrazol-3-yl,imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, pyrazin-2-yl,[1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl.

The compounds of the formula I may, depending on the substitutionpattern, contain one or more further centers of chirality. Accordingly,the compounds according to the invention can be present as pureenantiomers or diastereomers or as enantiomer or diastereomer mixtures.The invention provides both the pure enantiomers or diastereomers andtheir mixtures.

The compounds of the formula I may also be present in the form of theN-oxides and/or of their agriculturally useful salts, the type of saltgenerally not being important. Suitable salts are generally the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, have no adverse effect on the herbicidalactivity of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium or potassium, of the alkaline earth metals, preferablycalcium or magnesium, and of the transition metals, preferablymanganese, copper, zinc or iron. Another cation that may be used isammonium, where, if desired, one to four hydrogen atoms may be replacedby C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropyl-ammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium. Another suitableammonium cation is the pyridine nitrogen atom of the formula Iquaternized by alkylation or arylation. Also suitable are phosphoniumions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, orsulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of suitable acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and also the anions of C₁-C₄-alkanoicacids, preferably formate, acetate, propionate, butyrate ortrifluoroacetate.

With respect to the variables, the particularly preferred embodiments ofthe intermediates correspond to those of the groups of the formula I.

In a particular embodiment, the variables of the compounds of theformula I have the following meanings, these meanings, both on their ownand in combination with one another, being particular embodiments of thecompounds of the formula I:

In one preferred embodiment of the compounds of the formula I, A is Nand E, G and M are C—R^(c). These compounds correspond to the formulaI.1

in which the groups R^(c2), R^(c3) and R^(c4) each correspond to a groupR^(c) and preferably have the following meanings:

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃;

R^(c3) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^(c4) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.

In particularly preferred embodiments of the compounds of the formula Iand in particular those of the formula I.1, R¹ is selected from thegroup consisting of OH, OCH₃, OC(O)CH₃, OC(O)CH₂CH₃, OC(O)CH(CH₃)₂,OC(O)C(CH₃)₃, OC(O)-c-C₃H₅, OC(O)—C₆H₅, OC(O)—CH₂C₆H₅, OC(O)CH₂Cl,OC(O)—CF₃, OC(O)—CH₂OCH₃, OC(O)—N(CH₃)₂ and OC(O)—OCH₂CH₃.

In particularly preferred embodiments of the compounds of the formula Iand in particular those of the formula I.1, R² is phenyl which issubstituted by a group selected from the group consisting of 2-Br, 2-Cl,2,4-Cl₂, 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF₃, 2-Cl-5-CF₃,2-Cl-6-CF₃, 2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂, 2,6-F₂, 2-F-4-CF₃,2-F-5-CF₃, 2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F, 2-NO₂-5-F, 2-NO₂-6-F,2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃, 2-NO₂-3,6-F₂, 2-CN, 2-CH₃,2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃, 2-CH₃-5-CF₃, 2-CH₃-6-CF₃,2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F, 2-OCH₃-6-F, 2-OCH₃-4-CF₃,2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂, 2-CHF₂, 2-CHF₂-4-F,2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF2-4-CF₃, 2-CHF₂-5-CF₃, 2-CHF₂-6-CF₃,2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F, 2-CF₃-4-CF₃,2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂, 2-OCHF₂-4-F,2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃, 2-OCHF₂-6-CF₃,2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F, 2-OCF₃-6-F,2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃ and 2-OCF₃-3,6-F₂.

In particularly preferred embodiments of the compounds of the formula Iand in particular those of the formula I.1, X is selected from the groupconsisting of oxygen and sulfur.

In particularly preferred embodiments of the compounds of the formula Iand in particular those of the formula I.1, Y is selected from the groupconsisting of oxygen and sulfur.

In a further embodiment of the compounds of the formula I, A, G and Mare C—R^(c) and E is N. These compounds correspond to the formula I.2

in which the groups R^(c1), R^(c3) and R^(c4) each correspond to a groupR^(c).

In a further embodiment of the compounds of the formula I, A, E and Mare C—R^(c) and G is N. These compounds correspond to the formula I.3

in which the groups R^(c1), R^(c2) and R^(c4) each correspond to a groupR^(c) and preferably have the following meanings:

R^(d), is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl;

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃;

R^(c4) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃.

In a further embodiment of the compounds of the formula I, A, E and Gare C—R^(c) and M is N. These compounds correspond to the formula I.4

in which the groups R^(c1), R^(c2) and R^(c3) each correspond to a groupR^(c) and preferably have the following meanings:

R^(c1) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^(c2) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H;

R^(c3) is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H,Br, OH and OCH₃.

Particularly preferred aspects of the compounds of the formula I relateto those of each of the formulae I.1 to I.14 in which the variables havethe meanings preferred for formula I.

In a first preferred embodiment of the invention, R¹ is O—R^(A).

In a further preferred embodiment of the invention, R¹ is S(O)_(S)—R^(A)where n is preferably 0 or 2, in particular 2.

In a further preferred embodiment, R¹ is O—S(O)_(n)—R^(A), where n ispreferably 0 or 2, in particular 2, such as, for example, OS(O)₂—CH₃,OS(O)₂—C₂H₅, OS(O)₂—C₃H₇, OS(O)₂—C₆H₅ or OS(O)₂-(4-CH₃—C₆H₄).

In a further preferred embodiment, R¹ is O—S(O)_(n)—NR^(i)R^(ii), whichhas in particular the groups NR^(i)R^(ii) mentioned below as beingpreferred.

R^(A) is in particular H, C₁-C₆-alkylcarbonyl, such as C(O)CH₃,C(O)CH₂CH₃, C(O)CH(CH₃)₂ or C(O)C(CH₃)₃; C₁-C₆-cycloalkylcarbonyl, suchas cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl;C₂-C₆-alkenylcarbonyl, such as C(O)CH═CH₂ or C(O)CH₂CH═CH₂, optionallysubst. benzoyl, such as C(O)C₆H₅, C(O)[2-CH₃-C₆H₄], C(O)[4-CH₃—C₆H₄],C(O)[2-F—C₆H₄], C(O)[4-F—C₆H₄], or optionally subst. heteroaryl, such aspyridine, which is attached via a carbonyl group. Particularlypreferably, R^(A) is H or C₁-C₆-alkylcarbonyl.

More particularly preferably, R^(A) is selected from the groupconsisting of H, OCH₃, C(O)CH₃, C(O)CH₂CH₃, C(O)CH(CH₃)₂, C(O)C(CH₃)₃,C(O)-c-C₃H₅, C(O)—C₆H₅, C(O)—CH₂C₆H₅, C(O)CH₂Cl, C(O)CF₃, C(O)CH₂OCH₃,C(O)N(CH₃)₂ and C(O)OCH₂CH₃.

In a further preferred embodiment of the invention, R^(A) isNR^(i)R^(ii).

In a further preferred embodiment of the invention, R^(A) isZ—NR^(i)—C(O)—NRR^(ii), where R^(i) and R^(ii) are as defined at theoutset and preferably as defined below. In further embodiments,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and C₁-C₄-alkoxy-C₁-C₄-alkyl, inparticular OCH₃, OC₂H₅, CH₂CH₂OCH₃ and CH₂CH₂Cl, may also be possiblefor R^(i) and R^(ii), independently of one another.

R^(i) and R^(ii) are preferably C₁-C₈-alkyl, C₁-C₄-haloalkyl,Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z-phenyl,Z—C(═O)—R^(a) or Z-hetaryl. Here, preference is given to CH₃, C₂H₅,n-propyl, CH(CH₃)₂, butyl, 2-chloroethyl, cyclopentyl, cyclohexyl,2-ethoxymethyl, 2-chloroethoxy, phenyl, pyrimidines or triazines whoserings are unsubstituted or substituted. Here, preferred substituents areC₁-C₄-alkylcarbonyl or C₁-C₄-haloalkylcarbonyl, in particular C(═O)—CH₃,C(═O)—C₂H₅, C(═O)—C₃H₇, C(═O)—CH(CH₃)₂, butylcarbonyl and C(═O)—CH₂Cl.Particularly preferred aspects of the group NR^(i)R^(ii) areN(di-C₁-C₄-alkyl), in particular N(CH₃)—C₁-C₄-alkyl, such as N(CH₃)₂,N(CH₃)CH₂CH₃, N(CH₃)C₃H₇ and N(CH₃)CH(CH₃)₂.

Further particularly preferred aspects of NR^(i)R^(ii) are NH-aryl,where aryl is preferably phenyl which is substituted—in particular inthe 2- and 6-position—by one to three identical or different halogen,CH₃, halo-C₁-C₂-alkyl, halo-C₁-C₂-alkoxy and carboxyl groups, such as2-Cl, 6-COOH—C₆H₃, 2,6-Cl₂-C₆H₃, 2,6-F₂—C₆H₃, 2,6-Cl₂ 3-C₆H₂,2-CF₃,6-CH₂CHF₂—C₆H₃, 2-CF₃,6-OCF₃—C₆H₃ and 2-CF₃,6-CH₂CHF₂—C₆H₃.

Further aspects of NR^(i)R^(ii) are NH-heteroaryl, where heteroaryl ispreferably one of the preferred heteroaromatic groups below, inparticular triazinyl, pyrimidinyl or triazolopyrimidinyl, such as[1,2,4]triazolo[1,5-a]pyrimidin-2-yl, which groups may be substituted,in particular by C₁-C₄-alkoxy and/or halogen. Particular preference isgiven to 5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl,5,7-diethoxy-[1,2,4]-triazolo[1,5-a]pyrimidin-2-yl,5-fluoro-7-methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl and5-fluoro-7-ethoxy-[1,2,4]-triazolo[1,5-a]pyrimidin-2-yl.

In a further preferred embodiment of the invention, R^(A) is a 5- or6-membered heterocycle optionally substituted by R^(b) as defined above,which preferably has either 1, 2, 3 or 4 nitrogen atoms or 1 oxygen or 1sulfur atom and if appropriate 1 or 2 nitrogen atoms as ring members andwhich is unsubstituted or may have 1 or 2 substituents selected fromR^(b). Preference is given to saturated or unsaturated groups attachedvia nitrogen, such as, for example:

Heteroaromatic groups: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 2-furyl, 3-furyl,2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl,isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl,imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl,thiazol-4-yl and thiazol-5-yl;

In another aspect, R^(A) is a heteroaromatic group attached via carbon,such as pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl,thiazol-4-yl, thiazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl,pyrazin-2-yl, [1H]-tetrazol-5-yl and [2H]-tetrazol-5-yl, where each ofthe heterocycles mentioned here in an exemplary manner may have 1 or 2substituents selected from R^(b). Preferred groups R^(b) are inparticular F, Cl, CN, NO₂, CH₃, C₂H₅, OCH₃, OC₂H₅, OCHF2, OCF₃ and CF₃.

In a further preferred aspect, R² is phenyl which is unsubstituted orpartially or fully substituted by groups R^(b). Particular preference isgiven to compounds in which a group R^(b) is located in theortho-position. Such compounds of the formula I are described by theformula I.A:

In formula I.A, the index m is zero or an integer from one to four,preferably 0, 1 or 2, in particular 0 or 1. R⁵ and R⁶ are groups R^(b)as defined at the outset, preferably halogen, NO₂, C₁-C₂-haloalkyl andC₁-C₄-alkoxy. One group R⁶ is preferably located in position 5. A groupR⁶ in position 3 is a further preferred embodiment.

Particularly preferably, R⁵ is Br, F, NO₂, CN, CH₃, OCH₃, CHF₂ or OCHF₂.R⁶ is particularly preferably halogen or halomethyl, such as Cl, F orCF₃. Especially preferably, (R⁶)_(m) is selected from the groupconsisting of 4-F, 5-F, 6-F, 4-CF₃,5-CF₃ and 3,6-F₂.

In a preferred embodiment, X is O.

In a further embodiment, X is S.

In a further embodiment, X is NR³.

In a preferred embodiment, Y is O.

In a further embodiment, Y is S.

R³ is preferably H, C₁-C₆-alkyl, such as CH₃, C₂H₅, n-C₃H₇, CH(CH₃)₂,n-C₃H₉, or C(CH₃)₃; C₃-C₆-cycloalkyl-C₁-C₄-alkyl, such ascyclopropylmethyl, C₃-C₆-alkenyl, such as CH₂CH═CH₂, CH₂C(CH₃)═CH₂,CH₂CH₂H═CH₂, CH₂CH₂C(CH₃)—CH₂, CH₂CH₂CH₂CH═CH₂, CH₂CH₂CH₂C(CH₃)═CH₂, oroptionally subst. phenyl, such as C₆H₅, 4-CH₃—C₆H₄, 4-F—C₆H₄ orS(O)_(n)—R^(N), where R^(N) is C₁-C₆-haloalkyl, such as CH₂CF₃, CH₂CHF₂.

A further embodiment relates to the N-oxides of the compounds of theformula I.

A further embodiment relates to salts of the compounds of the formula I,in particular those which are obtainable by quaternization of thepyridine nitrogen atom, which may preferably take place by alkylation orarylation of the compounds of the formula I. Preferred salts of thecompounds are thus the N-alkyl salts, in particular the N-methyl salts,and the N-phenyl salts.

In particular with a view to their use, preference is given to thecompounds of the formula I compiled in the tables below, which compoundscorrespond to the formula I.1A. The groups mentioned for a substituentin the tables are furthermore per se, independently of the combinationin which they are mentioned, a particularly preferred aspect of thesubstituent in question.

Table 1

Compounds of the formula I in which X and Y are O, the index m in(R⁶)_(m) is zero and the combination of R¹ and R⁵ for a compoundcorresponds in each case to one row of Table A

Table 2

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 4-Clandthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 3

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 3-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 4

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 4-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 5

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 5-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 6

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 6-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 7

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 4-CF₃ andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 8

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 5-CF₃ andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 9

Compounds of the formula I in which X and Y are O, (R⁶)_(m) is 3,6-F₂and the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 10

Compounds of the formula I in which X is O and Y is S, the index m in(R⁶)_(m) is zero and the combination of R¹ and R⁵ for a compoundcorresponds in each case to one row of Table A

Table 11

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is4-Cland the combination of R¹ and R⁵ for a compound corresponds in eachcase to one row of Table A

Table 12

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is 3-Fand the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 13

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is 4-Fand the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 14

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is 5-Fand the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 15

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is 6-Fand the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 16

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is 4-CF₃and the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 17

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is 5-CF₃and the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 18

Compounds of the formula I in which X is O and Y is S, (R⁶)_(m) is3,6-F₂ and the combination of R¹ and R⁵ for a compound corresponds ineach case to one row of Table A

Table 19

Compounds of the formula I in which X and Y are S, the index m in(R⁶)_(m) is zero and the combination of R¹ and R⁵ for a compoundcorresponds in each case to one row of Table A

Table 20

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 4-Clandthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 21

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 3-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 22

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 4-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 23

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 5-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 24

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 6-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 25

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 4-CF₃ andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 26

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 5-CF₃ andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 27

Compounds of the formula I in which X and Y are S, (R⁶)_(m) is 3,6-F₂and the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 28

Compounds of the formula I in which X is S and Y is O, the index m in(R⁶), is zero and the combination of R¹ and R⁵ for a compoundcorresponds in each case to one row of Table A

Table 29

Compounds of the formula I in which X is S and Y is O, (R⁶)_(m) is4-Cland the combination of R¹ and R⁵ for a compound corresponds in eachcase to one row of Table A

Table 30

Compounds of the formula I in which X is S and Y is O, (R⁶), is 3-F andthe combination of R¹ and R⁵ for a compound corresponds in each case toone row of Table A

Table 31

Compounds of the formula I in which X is S and Y is O, (R⁶)_(m) is 4-Fand the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 32

Compounds of the formula I in which X is S and Y is O, (R⁶)_(m) is 5-Fand the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 33

Compounds of the formula I in which X is S and Y is O, (R⁶)_(m) is 6-Fand the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 34

Compounds of the formula I in which X is S and Y is O, (R⁶)_(m) is 4-CF₃and the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 35

Compounds of the formula I in which X is S and Y is O, (R⁶)_(m) is 5-CF₃and the combination of R¹ and R⁵ for a compound corresponds in each caseto one row of Table A

Table 36

Compounds of the formula I in which X is S and Y is O, (R⁶)_(m) is3,6-F₂ and the combination of R¹ and R⁵ for a compound corresponds ineach case to one row of Table A

TABLE A Compounds of the formula I which correspond to the formula I.1AI.1A

No. R¹ R⁵ A-1 OH Br A-2 OCH₃ Br A-3 OC(O)CH₃ Br A-4 OC(O)CH₂CH₃ Br A-5OC(O)CH(CH₃)₂ Br A-6 OC(O)C(CH₃)₃ Br A-7 OC(O)—c-C₃H₅ Br A-8 OC(O)—C₆H₅Br A-9 OC(O)—CH₂C₆H₅ Br A-10 OC(O)CH₂Cl Br A-11 OC(O)—CF₃ Br A-12OC(O)—CH₂OCH₃ Br A-13 OC(O)—N(CH₃)₂ Br A-14 OC(O)—OCH₂CH₃ Br A-15OS(O)₂—CH₃ Br A-16 OS(O)₂—C₂H₅ Br A-17 OS(O)₂—C₃H₇ Br A-18OS(O)₂—CH(CH₃)₂ Br A-19 OS(O)₂—C₆H₅ Br A-20 OS(O)₂-T1 Br A-21 OS(O)₂—T2Br A-22 OS(O)₂—T3 Br A-23 OS(O)₂—T4 Br A-24 OS(O)₂—T5 Br A-25 OS(O)₂-T6Br A-26 OS(O)₂-T7 Br A-27 OS(O)₂-T8 Br A-28 OS(O)₂-T9 Br A-29 OS(O)₂-T10Br A-30 OS(O)₂-T11 Br A-31 OS(O)₂-T12 Br A-32 OH Cl A-33 OCH₃ Cl A-34OC(O)CH₃ Cl A-35 OC(O)CH₂CH₃ Cl A-36 OC(O)CH(CH₃)₂ Cl A-37 OC(O)C(CH₃)₃Cl A-38 OC(O) c-C₃H₅ Cl A-39 OC(O)—C₆H₅ Cl A-40 OC(O)—CH₂C₆H₅ Cl A-41OC(O)CH₂Cl Cl A-42 OC(O)—CF₃ Cl A-43 OC(O)—CH₂OCH₃ Cl A-44 OC(O)—N(CH₃)₂Cl A-45 OC(O)—OCH₂CH₃ Cl A-46 OS(O)₂—CH₃ Cl A-47 OS(O)₂—C₂H₅ Cl A-48OS(O)₂—C₃H₇ Cl A-49 OS(O)₂—CH(CH₃)₂ Cl A-50 OS(O)₂—C₆H₅ Cl A-51OS(O)₂-T1 Cl A-52 OS(O)₂ T2 Cl A-53 OS(O)₂ T3 Cl A-54 OS(O)₂ T4 Cl A-55OS(O)₂ T5 Cl A-56 OS(O)₂-T6 Cl A-57 OS(O)₂-T7 Cl A-58 OS(O)₂-T8 Cl A-59OS(O)₂-T9 Cl A-60 OS(O)₂-T10 Cl A-61 OS(O)₂-T11 Cl A-62 OS(O)₂-T12 ClA-63 OH F A-64 OCH₃ F A-65 OC(O)CH₃ F A-66 OC(O)CH₂CH₃ F A-67OC(O)CH(CH₃)₂ F A-68 OC(O)C(CH₃)₃ F A-69 OC(O) c-C₃H₅ F A-70 OC(O)—C₆H₅F A-71 OC(O)—CH₂C₆H₅ F A-72 OC(O)CH₂Cl F A-73 OC(O)—CF₃ F A-74OC(O)—CH₂OCH₃ F A-75 OC(O)—N(CH₃)₂ F A-76 OC(O)—OCH₂CH₃ F A-77OS(O)₂—CH₃ F A-78 OS(O)₂—C₂H₅ F A-79 OS(O)₂—C₃H₇ F A-80 OS(O)₂—CH(CH₃)₂F A-81 OS(O)₂—C₆H₅ F A-82 OS(O)₂-T1 F A-83 OS(O)₂ T2 F A-84 OS(O)₂ T3 FA-85 OS(O)₂ T4 F A-86 OS(O)₂ T5 F A-87 OS(O)₂-T6 F A-88 OS(O)₂-T7 F A-89OS(O)₂-T8 F A-90 OS(O)₂-T9 F A-91 OS(O)₂-T10 F A-92 OS(O)₂-T11 F A-93OS(O)₂-T12 F A-94 OH NO₂ A-95 OCH₃ NO₂ A-96 OC(O)CH₃ NO₂ A-97OC(O)CH₂CH₃ NO₂ A-98 OC(O)CH(CH₃)₂ NO₂ A-99 OC(O)C(CH₃)₃ NO₂ A-100OC(O) c-C₃H₅ NO₂ A-101 OC(O)—C₆H₅ NO₂ A-102 OC(O)—CH₂C₆H₅ NO₂ A-103OC(O)CH₂Cl NO₂ A-104 OC(O)—CF₃ NO₂ A-105 OC(O)—CH₂OCH₃ NO₂ A-106OC(O)—N(CH₃)₂ NO₂ A-107 OC(O)—OCH₂CH₃ NO₂ A-108 OS(O)₂—CH₃ NO₂ A-109OS(O)₂—C₂H₅ NO₂ A-110 OS(O)₂—C₃H₇ NO₂ A-111 OS(O)₂—CH(CH₃)₂ NO₂ A-112OS(O)₂—C₆H₅ NO₂ A-113 OS(O)₂-T1 NO₂ A-114 OS(O)₂ T2 NO₂ A-115 OS(O)₂ T3NO₂ A-116 OS(O)₂ T4 NO₂ A-117 OS(O)₂ T5 NO₂ A-118 OS(O)₂-T6 NO₂ A-119OS(O)₂-T7 NO₂ A-120 OS(O)₂-T8 NO₂ A-121 OS(O)₂-T9 NO₂ A-122 OS(O)₂-T10NO₂ A-123 OS(O)₂-T11 NO₂ A-124 OS(O)₂-T12 NO₂ A-125 OH CN A-126 OCH₃ CNA-127 OC(O)CH₃ CN A-128 OC(O)CH₂CH₃ CN A-129 OC(O)CH(CH₃)₂ CN A-130OC(O)C(CH₃)₃ CN A-131 OC(O) c-C₃H₅ CN A-132 OC(O)—C₆H₅ CN A-133OC(O)—CH₂C₆H₅ CN A-134 OC(O)CH₂Cl CN A-135 OC(O)—CF₃ CN A-136OC(O)—CH₂OCH₃ CN A-137 OC(O)—N(CH₃)₂ CN A-138 OC(O)—OCH₂CH₃ CN A-139OS(O)₂—CH₃ CN A-140 OS(O)₂—C₂H₅ CN A-141 OS(O)₂—C₃H₇ CN A-142OS(O)₂—CH(CH₃)₂ CN A-143 OS(O)₂—C₆H₅ CN A-144 OS(O)₂-T1 CN A-145OS(O)₂ T2 CN A-146 OS(O)₂ T3 CN A-147 OS(O)₂ T4 CN A-148 OS(O)₂ T5 CNA-149 OS(O)₂-T6 CN A-150 OS(O)₂-T7 CN A-151 OS(O)₂-T8 CN A-152 OS(O)₂-T9CN A-153 OS(O)₂-T10 CN A-154 OS(O)₂-T11 CN A-155 OS(O)₂-T12 CN A-156 OHCH₃ A-157 OCH₃ CH₃ A-158 OC(O)CH₃ CH₃ A-159 OC(O)CH₂CH₃ CH₃ A-160OC(O)CH(CH₃)₂ CH₃ A-161 OC(O)C(CH₃)₃ CH₃ A-162 OC(O) c-C₃H₅ CH₃ A-163OC(O)—C₆H₅ CH₃ A-164 OC(O)—CH₂C₆H₅ CH₃ A-165 OC(O)CH₂Cl CH₃ A-166OC(O)—CF₃ CH₃ A-167 OC(O)—CH₂OCH₃ CH₃ A-168 OC(O)—N(CH₃)₂ CH₃ A-169OC(O)—OCH₂CH₃ CH₃ A-170 OS(O)₂—CH₃ CH₃ A-171 OS(O)₂—C₂H₅ CH₃ A-172OS(O)₂—C₃H₇ CH₃ A-173 OS(O)₂—CH(CH₃)₂ CH₃ A-174 OS(O)₂—C₆H₅ CH₃ A-175OS(O)₂-T1 CH₃ A-176 OS(O)₂ T2 CH₃ A-177 OS(O)₂ T3 CH₃ A-178 OS(O)₂ T4CH₃ A-179 OS(O)₂ T5 CH₃ A-180 OS(O)₂-T6 CH₃ A-181 OS(O)₂-T7 CH₃ A-182OS(O)₂-T8 CH₃ A-183 OS(O)₂-T9 CH₃ A-184 OS(O)₂-T10 CH₃ A-185 OS(O)₂-T11CH₃ A-186 OS(O)₂-T12 CH₃ A-187 OH OCH₃ A-188 OCH₃ OCH₃ A-189 OC(O)CH₃OCH₃ A-190 OC(O)CH₂CH₃ OCH₃ A-191 OC(O)CH(CH₃)₂ OCH₃ A-192 OC(O)C(CH₃)₃OCH₃ A-193 OC(O) c-C₃H₅ OCH₃ A-194 OC(O)—C₆H₅ OCH₃ A-195 OC(O)—CH₂C₆H₅OCH₃ A-196 OC(O)CH₂Cl OCH₃ A-197 OC(O)—CF₃ OCH₃ A-198 OC(O)—CH₂OCH₃ OCH₃A-199 OC(O)—N(CH₃)₂ OCH₃ A-200 OC(O)—OCH₂CH₃ OCH₃ A-201 OS(O)₂—CH₃ OCH₃A-202 OS(O)₂—C2H₅ OCH₃ A-203 OS(O)₂—C₃H₇ OCH₃ A-204 OS(O)₂—CH(CH₃)₂ OCH₃A-205 OS(O)₂—C₆H₅ OCH₃ A-206 OS(O)₂-T1 OCH₃ A-207 OS(O)₂ T2 OCH₃ A-208OS(O)₂ T3 OCH₃ A-209 OS(O)₂ T4 OCH₃ A-210 OS(O)₂ T5 OCH₃ A-211 OS(O)₂-T6OCH₃ A-212 OS(O)₂-T7 OCH₃ A-213 OS(O)₂-T8 OCH₃ A-214 OS(O)₂-T9 OCH₃A-215 OS(O)₂-T10 OCH₃ A-216 OS(O)₂-T11 OCH₃ A-217 OS(O)₂-T12 OCH₃ A-218OH CHF₂ A-219 OCH₃ CHF₂ A-220 OC(O)CH₃ CHF₂ A-221 OC(O)CH₂CH₃ CHF₂ A-222OC(O)CH(CH₃)₂ CHF₂ A-223 OC(O)C(CH₃)₃ CHF₂ A-224 OC(O) c-C₃H₅ CHF₂ A-225OC(O)—C₆H₅ CHF₂ A-226 OC(O)—CH₂C₆H₅ CHF₂ A-227 OC(O)CH₂Cl CHF₂ A-228OC(O)—CF₃ CHF₂ A-229 OC(O)—CH₂OCH₃ CHF₂ A-230 OC(O)—N(CH₃)₂ CHF₂ A-231OC(O)—OCH₂CH₃ CHF₂ A-232 OS(O)₂—CH₃ CHF₂ A-233 OS(O)₂—C₂H₅ CHF₂ A-234OS(O)₂—C₃H₇ CHF₂ A-235 OS(O)₂—CH(CH₃)₂ CHF₂ A-236 OS(O)₂—C₆H₅ CHF₂ A-237OS(O)₂-T1 CHF₂ A-238 OS(O)₂ T2 CHF₂ A-239 OS(O)₂ T3 CHF₂ A-240 OS(O)₂ T4CHF₂ A-241 OS(O)₂ T5 CHF₂ A-242 OS(O)₂-T6 CHF₂ A-243 OS(O)₂-T7 CHF₂A-244 OS(O)₂-T8 CHF₂ A-245 OS(O)₂-T9 CHF₂ A-246 OS(O)₂-T10 CHF₂ A-247OS(O)₂-T11 CHF₂ A-248 OS(O)₂-T12 CHF₂ A-249 OH CF₃ A-250 OCH₃ CF₃ A-251OC(O)CH₃ CF₃ A-252 OC(O)CH₂CH₃ CF₃ A-253 OC(O)CH(CH₃)₂ CF₃ A-254OC(O)C(CH₃)₃ CF₃ A-255 OC(O) c-C₃H₅ CF₃ A-256 OC(O)—C₆H₅ CF₃ A-257OC(O)—CH₂C₆H₅ CF₃ A-258 OC(O)CH₂Cl CF₃ A-259 OC(O)—CF₃ CF₃ A-260OC(O)—CH₂OCH₃ CF₃ A-261 OC(O)—N(CH₃)₂ CF₃ A-262 OC(O)—OCH₂CH₃ CF₃ A-263OS(O)₂—CH₃ CF₃ A-264 OS(O)₂—C₂H₅ CF₃ A-265 OS(O)₂—C₃H₇ CF₃ A-266OS(O)₂—CH(CH₃)₂ CF₃ A-267 OS(O)₂—C₆H₅ CF₃ A-268 OS(O)₂-T1 CF₃ A-269OS(O)₂ T2 CF₃ A-270 OS(O)₂ T3 CF₃ A-271 OS(O)₂ T4 CF₃ A-272 OS(O)₂ T5CF₃ A-273 OS(O)₂-T6 CF₃ A-274 OS(O)₂-T7 CF₃ A-275 OS(O)₂-T8 CF₃ A-276OS(O)₂-T9 CF₃ A-277 OS(O)₂-T10 CF₃ A-278 OS(O)₂-T11 CF₃ A-279 OS(O)₂-T12CF₃ A-280 OH OCHF₂ A-281 OCH₃ OCHF₂ A-282 OC(O)CH₃ OCHF₂ A-283OC(O)CH₂CH₃ OCHF₂ A-284 OC(O)CH(CH₃)₂ OCHF₂ A-285 OC(O)C(CH₃)₃ OCHF₂A-286 OC(O) c-C₃H₅ OCHF₂ A-287 OC(O)—C₆H₅ OCHF₂ A-288 OC(O)—CH₂C₆H₅OCHF₂ A-289 OC(O)CH₂Cl OCHF₂ A-290 OC(O)—CF₃ OCHF₂ A-291 OC(O)—CH₂OCH₃OCHF₂ A-292 OC(O)—N(CH₃)₂ OCHF₂ A-293 OC(O)—OCH₂CH₃ OCHF₂ A-294OS(O)₂—CH₃ OCHF₂ A-295 OS(O)₂—C₂H₅ OCHF₂ A-296 OS(O)₂—C₃H₇ OCHF₂ A-297OS(O)₂—CH(CH₃)₂ OCHF₂ A-298 OS(O)₂—C₆H₅ OCHF₂ A-299 OS(O)₂-T1 OCHF₂A-300 OS(O)₂ T2 OCHF₂ A-301 OS(O)₂ T3 OCHF₂ A-302 OS(O)₂ T4 OCHF₂ A-303OS(O)₂ T5 OCHF₂ A-304 OS(O)₂-T6 OCHF₂ A-305 OS(O)₂-T7 OCHF₂ A-306OS(O)₂-T8 OCHF₂ A-307 OS(O)₂-T9 OCHF₂ A-308 OS(O)₂-T10 OCHF₂ A-309OS(O)₂-T11 OCHF₂ A-310 OS(O)₂-T12 OCHF₂ A-311 OH OCF₃ A-312 OCH₃ OCF₃A-313 OC(O)CH₃ OCF₃ A-314 OC(O)CH₂CH₃ OCF₃ A-315 OC(O)CH(CH₃)₂ OCF₃A-316 OC(O)C(CH₃)₃ OCF₃ A-317 OC(O) c-C₃H₅ OCF₃ A-318 OC(O)—C₆H₅ OCF₃A-319 OC(O)—CH₂C₆H₅ OCF₃ A-320 OC(O)CH₂Cl OCF₃ A-321 OC(O)—CF₃ OCF₃A-322 OC(O)—CH₂OCH₃ OCF₃ A-323 OC(O)—N(CH₃)₂ OCF₃ A-324 OC(O)—OCH₂CH₃OCF₃ A-325 OS(O)₂—CH₃ OCF₃ A-326 OS(O)₂—C₂H₅ OCF₃ A-327 OS(O)₂—C₃H₇ OCF₃A-328 OS(O)₂—CH(CH₃)₂ OCF₃ A-329 OS(O)₂—C₆H₅ OCF₃ A-330 OS(O)₂-T1 OCF₃A-331 OS(O)₂ T2 OCF₃ A-332 OS(O)₂ T3 OCF₃ A-333 OS(O)₂ T4 OCF₃ A-334OS(O)₂ T5 OCF₃ A-335 OS(O)₂-T6 OCF₃ A-336 OS(O)₂-T7 OCF₃ A-337 OS(O)₂-T8OCF₃ A-338 OS(O)₂-T9 OCF₃ A-339 OS(O)₂-T10 OCF₃ A-340 OS(O)₂-T11 OCF₃A-341 OS(O)₂-T12 OCF₃ T1 = 4-CH₃—C₆H₄ T2 = N(CH₃)₂ T3 = N(CH₃)CH₂CH₃ T4= N(CH₃)C₃H₇ T5 = N(CH₃)CH(CH₃)₂ T6 = 2-Cl, 6-COOH—C₆H₃ T7 =2,6-Cl₂—C₆H₃ T8 = 2,6-F₂—C₆H₃ T9 = 2,6-Cl₂, 3-CH₃—C₆H₂ T10 = 2-CF₃,6-CH₂CHF₂—C₆H₃ T11 = 2-CF₃, 6-OCF₃—C₆H₃ T12 = 2-CF₃, 6-OCH₂CHF₂—C₆H₃

The compounds I and their agriculturally useful salts are suitable, bothas isomer mixtures and in the form of the pure isomers, as herbicides.They are suitable as such or as an appropriately formulated composition.The herbicidal compositions comprising the compound I, in particular thepreferred aspects thereof, control vegetation on non-crop areas veryefficiently, especially at high rates of application. They act againstbroad-leaved weeds and weed grasses in crops such as wheat, rice, corn,soybeans and cotton without causing any significant damage to the cropplants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds I, inparticular the preferred aspects thereof, or compositions comprisingthem can additionally be employed in a further number of crop plants foreliminating unwanted plants. Examples of suitable crops are thefollowing:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera, Zea mays.

The term “crop plants” also includes plants which have been modified bybreeding, mutagenesis or genetic engineering. Genetically modifiedplants are plants whose genetic material has been modified in a mannerwhich does not occur under natural conditions by crossing, mutations ornatural recombination (i.e. reassembly of the genetic information).Here, in general, one or more genes are integrated into the geneticmaterial of the plant to improve the properties of the plant.

Accordingly, the term “crop plants” also includes plants which, bybreeding and genetic engineering, have acquired tolerance to certainclasses of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD)inhibitors, acetolactate synthase (ALS) inhibitors, such as, forexample, sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) orimidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO 01/82685,WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073),enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as,for example, glyphosate (see, for example, WO 92/00377), glutaminesynthetase (GS) inhibitors, such as, for example, glufosinate (see, forexample, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, forexample, U.S. Pat. No. 5,559,024).

Numerous crop plants, for example Clearfield® oilseed rape, tolerant toimidazolinones, for example imazamox, have been generated with the aidof classic breeding methods (mutagenesis). Crop plants such as soybeans,cotton, corn, beet and oilseed rape, resistant to glyphosate orglufosinate, which are available under the tradenames RoundupReady®(glyphosate) and Liberty Link® (glufosinate) have been generated withthe aid of genetic engineering methods.

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more toxins, for examplethose of the bacterial strain Bacillus ssp. Toxins which are produced bysuch genetically modified plants include, for example, insecticidalproteins of Bacillus spp., in particular B. thuringiensis, such as theendotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1,Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs),for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins ofnematode-colonizing bacteria, for example Photorhabdus spp. orXenorhabdus spp.; toxins of animal organisms, for example wasp, spideror scorpion toxins; fungal toxins, for example from Streptomycetes;plant lectins, for example from peas or barley; agglutinins; proteinaseinhibitors, for example trypsin inhibitors, serine protease inhibitors,patatin, cystatin or papain inhibitors, ribosome-inactivating proteins(RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin;steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase,ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysoneinhibitors, or HMG-CoA reductase; ion channel blockers, for exampleinhibitors of sodium channels or calcium channels; juvenile hormoneesterase; receptors of the diuretic hormone (helicokinin receptors);stilbene synthase, bibenzyl synthase, chitinases and glucanases. In theplants, these toxins may also be produced as pretoxins, hybrid proteinsor truncated or otherwise modified proteins. Hybrid proteins arecharacterized by a novel combination of different protein domains (see,for example, WO 2002/015701). Further examples of such toxins orgenetically modified plants which produce these toxins are disclosed inEP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO03/018810 and WO 03/052073. The methods for producing these geneticallymodified plants are known to the person skilled in the art anddisclosed, for example, in the publications mentioned above. Numerous ofthe toxins mentioned above bestow, upon the plants by which they areproduced, tolerance to pests from all taxonomic classes of arthropods,in particular to beetles (Coeleropta), dipterans (Diptera) andbutterflies (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants which produce one or more genes coding forinsecticidal toxins are described, for example, in the publicationsmentioned above, and some of them are commercially available, such as,for example, YieldGard® (corn varieties producing the toxin Cry1Ab),YieldGard® Plus (corn varieties which produce the toxins Cry1Ab andCry3Bb1), Starlink® (corn varieties which produce the toxin Cry9c),Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B(cotton varieties which produce the toxin Cry1Ac), Bollgard® I (cottonvarieties which produce the toxin Cry1Ac), Bollgard® II (cottonvarieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cottonvarieties which produce a VIP toxin); NewLeaf® (potato varieties whichproduce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®,Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta SeedsSAS, France (corn varieties which produce the toxin Cry1Ab and the PATenyzme), MIR604 from Syngenta Seeds SAS, France (corn varieties whichproduce a modified version of the toxin Cry3A, see WO 03/018810), MON863 from Monsanto Europe S.A., Belgium (corn varieties which produce thetoxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cottonvarieties which produce a modified version of the toxin Cry1Ac) and 1507from Pioneer Overseas Corporation, Belgium (corn varieties which producethe toxin Cry1F and the PAT enzyme).

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more proteins which are morerobust or have increased resistance to bacterial, viral or fungalpathogens, such as, for example, pathogenesis.: related proteins (PRproteins, see EP-A 0 392 225), resistance proteins (for example potatovarieties producing two resistance genes against Phytophthora infestansfrom the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (forexample potato cultivars which, by producing this protein, are resistantto bacteria such as Erwinia amylvora).

Accordingly, the term “crop plants” also includes plants whoseproductivity has been improved with the aid of genetic engineeringmethods, for example by enhancing the potential yield (for examplebiomass, grain yield, starch, oil or protein content), tolerance todrought, salt or other limiting environmental factors or resistance topests and fungal, bacterial and viral pathogens.

The term “crop plants” also includes plants whose ingredients have beenmodified with the aid of genetic engineering methods in particular forimproving human or animal diet, for example by oil plants producinghealth-promoting long-chain omega 3 fatty acids or monounsaturated omega9 fatty acids (for example Nexera® oilseed rape).

The term “crop plants” also includes plants which have been modifiedwith the aid of genetic engineering methods for improving the productionof raw materials, for example by increasing the amylopectin content ofpotatoes (Amflora® potato).

Furthermore, it has been found that the compounds of the formula I arealso suitable for the defoliation and/or desiccation of plant parts, forwhich crop plants such as cotton, potato, oilseed rape, sunflower,soybean or field beans, in particular cotton, are suitable. In thisregard, there have been found compositions for the desiccation and/ordefoliation of plants, processes for preparing these compositions andmethods for desiccating and/or defoliating plants using the compounds ofthe formula I.

As desiccants, the compounds of the formula I are particularly suitablefor desiccating the above-ground parts of crop plants such as potato,oilseed rape, sunflower and soybean, but also cereals. This makespossible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is madepossible by concentrating within a certain period of time thedehiscence, or reduction of adhesion to the tree, in citrus fruit,olives and other species and varieties of pomaceous fruit, stone fruitand nuts. The same mechanism, i.e. the promotion of the development ofabscission tissue between fruit part or leaf part and shoot part of theplants is also essential for the readily controllable defoliation ofuseful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individualcotton plants mature leads to an increased fiber quality afterharvesting.

The compounds I, or the herbicidal compositions comprising the compoundsI, can be used, for example, in the form of ready-to-spray aqueoussolutions, powders, suspensions, also highly concentrated aqueous, oilyor other suspensions or dispersions, emulsions, oil dispersions, pastes,dusts, materials for broadcasting, or granules, by means of spraying,atomizing, dusting, spreading, watering or treatment of the seed ormixing with the seed. The use forms depend on the intended purpose; ineach case, they should ensure the finest possible distribution of theactive ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I, and auxiliaries which are customary for the formulation of cropprotection agents.

Examples of auxiliaries customary for the formulation of crop protectionagents are inert auxiliaries, solid carriers, surfactants (such asdispersants, protective colloids, emulsifiers, wetting agents andtackifiers), organic and inorganic thickeners, bactericides, antifreezeagents, antifoams, if appropriate colorants and, for seed formulations,adhesives.

Examples of thickeners (i.e. compounds which impart to the formulationmodified flow properties, i.e. high viscosity in the state of rest andlow viscosity in motion) are polysaccharides, such as xanthan gum(Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such asAttaclay® (from Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example,Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols,fatty acids, salts of fatty acids, organofluorine compounds and mixturesthereof.

Bactericides can be added for stabilizing the aqueous herbicidalformulation. Examples of bactericides are bactericides based ondichlorophen and benzyl alcohol hemiformal (Proxel® from ICI orActicide® R^(S) from Thor Chemie and Kathon® MK from Rohm & Haas), andalso isothiazolinone derivates, such as alkylisothiazolinones andbenzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol,urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments andwater-soluble dyes. Examples which may be mentioned are the dyes knownunder the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1,and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2,pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13,pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1,pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25,basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14,acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate,polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone or strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Solid carriers are mineral earths such as silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate andmagnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersantsand also emulsifiers) are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, for examplelignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonicacids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) anddibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignosulfite wasteliquors and proteins, denatured proteins, polysaccharides (e.g.methylcellulose), hydrophobically modified starches, polyvinyl alcohol(Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types),polyalkoxylates, polyvinylamine (BASF SE, Lupamine types),polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone andcopolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thecompounds of the formula I or Ia, either as such or dissolved in an oilor solvent, can be homogenized in water by means of a wetting agent,tackifier, dispersant or emulsifier. Alternatively, it is also possibleto prepare concentrates comprising active substance, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil,which are suitable for dilution with water.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight of at least one active compound. The active compounds areemployed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The compounds I of the invention can for example be formulated asfollows:

1. Products for dilution with water

A Water-soluble concentrates

10 parts by weight of active compound are dissolved in 90 parts byweight of water or a water-soluble solvent. As an alternative, wettersor other adjuvants are added. The active compound dissolves upondilution with water. This gives a formulation with an active compoundcontent of 10% by weight.

B Dispersible concentrates

20 parts by weight of active compound are dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion. The active compound content is 20% by weight.

C Emulsifiable concentrates

15 parts by weight of active compound are dissolved in 75 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). Dilution with water gives an emulsion. Theformulation has an active compound content of 15% by weight.

D Emulsions

25 parts by weight of active compound are dissolved in 35 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). This mixture is introduced into 30 parts by weightof water by means of an emulsifier (e.g. Ultraturrax) and made into ahomogeneous emulsion. Dilution with water gives an emulsion. Theformulation has an active compound content of 25% by weight.

E Suspensions

In an agitated ball mill, 20 parts by weight of active compound arecomminuted with addition of 10 parts by weight of dispersants andwetters and 70 parts by weight of water or an organic solvent to give afine active compound suspension. Dilution with water gives a stablesuspension of the active'compound. The active compound content in theformulation is 20% by weight.

F Water-dispersible granules and water-soluble granules

50 parts by weight of active compound are ground finely with addition of50 parts by weight of dispersants and wetters and made intowater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound.The formulation has an active compound content of 50% by weight.

G Water-dispersible powders and water-soluble powders

75 parts by weight of active compound are ground in a rotor-stator millwith addition of 25 parts by weight of dispersants, wetters and silicagel. Dilution with water gives a stable dispersion or solution of theactive compound. The active compound content of the formulation is 75%by weight.

H Gel formulations

In a ball mill, 20 parts by weight of active compound, 10 parts byweight of dispersant, 1 part by weight of gelling agent and 70 parts byweight of water or of an organic solvent are ground to give a finesuspension. Dilution with water gives a stable suspension with activecompound content of 20% by weight.

2. Products to be applied undiluted

I Dusts

5 parts by weight of active compound are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dusting powder with an active compound content of 5% by weight.

J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associatedwith 99.5 parts by weight of carriers. Current methods here areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted with an active compound content of 0.5% by weight.

K ULV solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a productto be applied undiluted with an active compound content of 10% byweight.

The compounds I or the herbicidal compositions comprising them can beapplied pre- or post-emergence, or together with the seed of a cropplant. It is also possible to apply the herbicidal compositions oractive compounds by applying seed, pretreated with the herbicidalcompositions or active compounds, of a crop plant. If the activecompounds are less well tolerated by certain crop plants, applicationtechniques may be used in which the herbicidal compositions are sprayed,with the aid of the spraying equipment, in such a way that as far aspossible they do not come into contact with the leaves of the sensitivecrop plants, while the active compounds reach the leaves of undesirableplants growing underneath, or the bare soil surface (post-directed,lay-by).

In a further embodiment, the compounds of the formula I or theherbicidal compositions can be applied by treating seed.

The treatment of seed comprises essentially all procedures familiar tothe person skilled in the art (seed dressing, seed coating, seeddusting, seed soaking, seed film coating, seed multilayer coating, seedencrusting, seed dripping and seed pelleting) based on the compounds ofthe formula I according to the invention or the compositions preparedtherefrom. Here, the herbicidal compositions can be applied diluted orundiluted.

The term seed comprises seed of all types, such as, for example, corns,seeds, fruits, tubers, cuttings and similar forms. Here, preferably, theterm seed describes corns and seeds.

The seed used can be seed of the useful plants mentioned above, but alsothe seed of transgenic plants or plants obtained by customary breedingmethods.

The rates of application of active compound are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.To treat the seed, the compounds I are generally employed in amounts offrom 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of the formula I incombination with safeners. Safeners are chemical compounds which preventor reduce damage to useful plants without substantially affecting theherbicidal action of the compounds of the formula I on unwanted plants.They can be used both before sowing (for example in the treatment ofseed, or on cuttings or seedlings) and before or after the emergence ofthe useful plant. The safeners and the compounds of the formula I can beused simultaneously or in succession. Suitable safeners are, forexample, (quinolin-8-oxy)acetic acids,1-phenyl-5-haloalkyl-1/−/−1,2,4-triazole-3-carboxylic acids,1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids,4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides,alpha-oximinophenylacetonitriles, acetophenone oximes,4,6-dihalo-2-phenylpyrimidines,N-[[4-(aminocarbonyl)phenyl]-sulfonyl]-2-benzamides, 1,8-naphthalicanhydride, 2-halo-4-(haloalkyl)-5-thiazole-carboxylic acids,phosphorothiolates and O-phenyl N-alkylcarbamates and theiragriculturally useful salts and, provided that they have an acidfunction, their agriculturally useful derivatives, such as amides,esters and thioesters.

To broaden the activity spectrum and to obtain synergistic effects, thecompounds of the formula I can be mixed and jointly applied withnumerous representatives of other herbicidal or growth-regulating groupsof active compounds or with safeners. Suitable mixing partners are, forexample, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoricacid and its derivatives, aminotriazoles, anilides,aryloxy/heteroaryl-oxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinoline carboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivates, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- andheteroaryloxyphenoxypropionic esters, phenylacetic acid and itsderivatives, 2-phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides, uracils and alsophenylpyrazolines and isoxazolines and their derivatives.

Moreover, it may be useful to apply the compounds I alone or incombination with other herbicides or else also mixed with further cropprotection agents, jointly, for example with compositions forcontrolling pests or phytopathogenic fungi or bacteria. Also of interestis the miscibility with mineral salt solutions which are employed foralleviating nutritional and trace element deficiencies. Other additivessuch as nonphytotoxic oils and oil concentrates may also be added.

Examples of herbicides which can be used in combination with thepyridine compounds of the formula I according to the present inventionare:

b1) from the group of the lipid biosynthesis inhibitors:

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop,clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop,diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P,fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P,haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop,quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim,tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate,EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb,pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate andvernolate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl,bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl,chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl,cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone,flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron,metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone,propoxycarbazone-sodium, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid,pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium,pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,trifloxysulfuron, triflusulfuron, triflusulfuron-methyl andtritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil,bromofenoxim, bromoxynil and its salts and esters, chlorobromuron,chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham,desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron,fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon,isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron,metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat,paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor,phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn,thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chiomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin,2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)-methylsulfamoyl]benzamide(H-1; CAS 372137-35-4), ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(H-2; CAS 353292-31-6),N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-3; CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-4; CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl-phenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-5; CAS 452099-05-7) andN-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-6; CAS 45100-03-7);

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone,diflufenican, fluridone, fluorochloridone, flurtamone, isoxaflutole,mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, ternbotrione, topramezone,4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one(H-7; CAS 352010-68-5) and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8;CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium(sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate andglufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors: asulam;

b9) from the group of the mitose inhibitors:

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin,carbetamide, chlorpropham, chiorthal, chlorthal-dimethyl, dinitramine,dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor,dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet,mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide,napropamide, pethoxamid, piperophos, pretilachlor, propachlor,propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

Compounds of the formula 2:

in which the variables have the following meanings:

-   Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset,    which radicals may be substituted by one to three groups R^(aa);    R²¹,R²²,R²³,R²⁴ are H, halogen or C₁-C₄-alkyl; X is O or NH; N is 0    or 1.

Compounds of the formula 2 have in particular the following meanings:

-   Y is

where # denotes the bond to the skeleton of the molecule; and

-   R²¹,R²²,R²³,R²⁴ are H, Cl, F or CH₃; R²⁵ is halogen, C₁-C₄-alkyl or    C₁-C₄-haloalkyl; R²⁶ is C₁-C₄-alkyl; R²⁷ is halogen, C₁-C₄-alkoxy or    C₁-C₄-haloalkoxy; R²⁸ is H, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or    C₁-C₄-haloalkoxy; M is 0, 1, 2 or 3; X is oxygen; N is 0 or 1.

Preferred compounds of the formula 2 have the following meanings:

-   Y is

R²¹ is H; R²²,R²³ are F; R²⁴ is H or F; X is oxygen; N is 0 or 1.

Particularly preferred compounds of the formula 2 are:3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethane-sulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-1);3-{[5-(2,2-difluoro-ethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-2);4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl-methyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-3);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-4);4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoro-methyl-2H-[1,2,3]triazole(2-5);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-6);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoro-methyl-2H-[1,2,3]triazole(2-7);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-8);4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-9);

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters,aminopyralid and its salts such asaminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichiorpropand its salts and esters, dichlorprop-P and its salts andesters, fluoroxypyr, fluoroxypyr-butomethyl, fluoroxypyr-meptyl, MCPAand its salts and esters, MCPA-thioethyl, MCPB and its salts and esters,mecopropand its salts and esters, mecoprop-P and its salts and esters,picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6)and its salts and esters, triclopyr and its salts and esters, and5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr,diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol,chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet,difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron,endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol,flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan,maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide,methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone,pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS499223-49-3) and its salts and esters.

Examples of preferred safeners C are benoxacor, cloquintocet,cyometrinil, cyprosulfamide, dichiormid, dicyclonone, dietholate,fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,mefenpyr, mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(H-12; R-29148, CAS 52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are knownherbicides and safeners, see, for example, The Compendium of PesticideCommon Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke,R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart,1995. Further herbicidally active compounds are known from WO 96/26202,WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991and from W. Krämer et al. (ed.) “Modern Crop Protection Compounds”, Vol.1, Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 1-component compositioncomprising an active compound combination comprising at least onepyridine compound of the formula I and at least one further activecompound, preferably selected from the active compounds of groups b1 tob15, and at least one solid or liquid carrier and/or one or moresurfactants and, if desired, one or more further auxiliaries customaryfor crop protection compositions.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 2-component compositioncomprising a first component comprising at least one pyridine compoundof the formula I, a solid or liquid carrier and/or one or moresurfactants and a second component comprising at least one furtheractive compound selected from the active compounds of groups b1 to b15,a solid or liquid carrier and/or one or more surfactants, whereadditionally both components may also comprise further auxiliariescustomary for crop protection compositions.

In binary compositions comprising at least one compound of the formula Ias component A and at least one herbicide B, the weight ratio of theactive compounds A:B is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula Ias component A and at least one safener C, the weight ratio of theactive compounds A:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In ternary compositions comprising both at least one compound of theformula I as component A, at least one herbicide B and at least onesafener C, the relative parts by weight of the components A:B aregenerally in the range of from 1:1000 to 1000:1, preferably in the rangeof from 1:500 to 500:1, in particular in the range of from 1:250 to250:1 and particularly preferably in the range of from 1:75 to 75:1; theweight ratio of the components A:C is generally in the range of from1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, inparticular in the range of from 1:250 to 250:1 and particularlypreferably in the range of from 1:75 to 75:1; and the weight ratio ofthe components B:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1. Preferably, the weight ratio of the components A+B tothe component C is in the range of from 1:500 to 500:1, in particular inthe range of from 1:250 to 250:1 and particularly preferably in therange of from 1:75 to 75:1.

Examples of particularly preferred compositions according to theinvention comprising in each case one individualized compound of theformula I and one mixing partner or a mixing partner combination aregiven in Table B below.

A further aspect of the invention relates to the compositions B-1 toH-1227 listed in Table B below, where in each case one row of Table Bcorresponds to a herbicidal composition comprising one of the compoundsof the formula I individualized in the above description (component 1)and the further active compound from groups b1) to b15) and/or safener Cstated in each case in the row in question (component 2). The activecompounds in the compositions described are in each case preferablypresent in synergistically effective amounts.

TABLE B Herbicide(s) B Safener C B-1 clodinafop-propargyl — B-2cycloxydim — B-3 cyhalofop-butyl — B-4 fenoxaprop-P-ethyl — B-5pinoxaden — B-6 profoxydim — B-7 tepraloxydim — B-8 tralkoxydim — B-9esprocarb — B-10 prosulfocarb — B-11 thiobencarb — B-12 triallate — B-13bensulfuron-methyl — B-14 bispyribac-sodium — B-15 cyclosulfamuron —B-16 flumetsulam — B-17 flupyrsulfuron-methyl-sodium — B-18foramsulfuron — B-19 imazamox — B-20 imazapic — B-21 imazapyr — B-22imazaquin — B-23 imazethapyr — B-24 imazosulfuron — B-25iodosulfuron-methyl-sodium — B-26 mesosulfuron — B-27 nicosulfuron —B-28 penoxsulam — B-29 propoxycarbazone-sodium — B-30pyrazosulfuron-ethyl — B-31 pyroxsulam — B-32 rimsulfuron — B-33sulfosulfuron — B-34 thiencarbazone-methyl — B-35 tritosulfuron — B-362,4-D and its salts and esters — B-37 aminopyralid and its salts andesters — B-38 clopyralid and its salts and esters — B-39 dicamba and itssalts and esters — B-40 fluroxypyr-meptyl — B-41 quinclorac — B-42quinmerac — B-43 H-9 — B-44 diflufenzopyr — B-45 diflufenzopyr-sodium —B-46 clomazone — B-47 diflufenican — B-48 fluorochloridone — B-49isoxaflutol — B-50 mesotrione — B-51 picolinafen — B-52 sulcotrione —B-53 tefuryltrione — B-54 tembotrione — B-55 topramezone — B-56 HHH-7 —B-57 atrazine — B-58 diuron — B-59 fluometuron — B-60 hexazinone — B-61isoproturon — B-62 metribuzin — B-63 propanil — B-64 terbuthylazine —B-65 paraquat dichloride — B-66 flumioxazin — B-67 oxyfluorfen — B-68sulfentrazone — B-69 H-1 — B-70 H-2 — B-71 glyphosate — B-72glyphosate-isopropylammonium — B-73 glyphosate-trimesium (sulfosate) —B-74 glufosinate — B-75 glufosinate-ammonium — B-76 pendimethalin — B-77trifluralin — B-78 acetochlor — B-79 cafenstrole — B-80 dimethenamid-P —B-81 fentrazamide — B-82 flufenacet — B-83 mefenacet — B-84 metazachlor— B-85 metolachlor-S — B-86 pyroxasulfone — B-87 isoxaben — B-88 dymron— B-89 indanofan — B-90 oxaziclomefone — B-91 triaziflam — B-92atrazine + H-1 — B-93 atrazine + glyphosate — B-94 atrazine + mesotrione— B-95 atrazine + nicosulfuron — B-96 atrazine + tembotrione — B-97atrazine + topramezone — B-98 clomazone + glyphosate — B-99diflufenican + clodinafop-propargyl — B-100 diflufenican +fenoxaprop-P-ethyl — B-101 diflufenican + flupyrsulfuron-methyl-sodium —B-102 diflufenican + glyphosate — B-103 diflufenican +mesosulfuron-methyl — B-104 diflufenican + pinoxaden — B-105diflufenican + pyroxsulam — B-106 flumetsulam + glyphosate — B-107flumioxazin + glyphosate — B-108 imazapic + glyphosate — B-109imazethapyr + glyphosate — B-110 isoxaflutol + H-1 — B-111 isoxaflutol +glyphosate — B-112 metazachlor + H-1 — B-113 metazachlor + glyphosate —B-114 metazachlor + mesotrione — B-115 metazachlor + nicosulfuron —B-116 metazachlor + terbuthylazin — B-117 metazachlor + topramezone —B-118 metribuzin + glyphosate — B-119 pendimethalin + H-1 — B-120pendimethalin + clodinafop-propargyl — B-121 pendimethalin +fenoxaprop-P-ethyl — B-122 pendimethalin + flupyrsulfuron-methyl-sodium— B-123 pendimethalin + glyphosate — B-124 pendimethalin +mesosulfuron-methyl — B-125 pendimethalin + mesotrionee — B-126pendimethalin + nicosulfuron — B-127 pendimethalin + pinoxaden — B-128pendimethalin + pyroxsulam — B-129 pendimethalin + tembotrione — B-130pendimethalin + topramezone — B-131 pyroxasulfone + tembotrione — B-132pyroxasulfone + topramezone — B-133 sulfentrazone + glyphosate — B-134terbuthylazin + H-1 — B-135 terbuthylazin + foramsulfuron — B-136terbuthylazin + glyphosate — B-137 terbuthylazin + mesotrione — B-138terbuthylazin + nicosulfuron — B-139 terbuthylazin + tembotrione — B-140terbuthylazin + topramezone — B-141 trifluralin + glyphosate — B-142 —benoxacor B-143 — cloquintocet B-144 — cyprosulfamide B-145 — dichlormidB-146 — fenchlorazole B-147 — isoxadifen B-148 — mefenpyr B-149 — H-11B-150 — H-12 B-151 clodinafop-propargyl benoxacor B-152 cycloxydimbenoxacor B-153 cyhalofop-butyl benoxacor B-154 fenoxaprop-P-ethylbenoxacor B-155 pinoxaden benoxacor B-156 profoxydim benoxacor B-157tepraloxydim benoxacor B-158 tralkoxydim benoxacor B-159 esprocarbbenoxacor B-160 prosulfocarb benoxacor B-161 thiobencarb benoxacor B-162triallate benoxacor B-163 bensulfuron-methyl benoxacor B-164bispyribac-sodium benoxacor B-165 cyclosulfamuron benoxacor B-166flumetsulam benoxacor B-167 flupyrsulfuron-methyl-sodium benoxacor B-168foramsulfuron benoxacor B-169 imazamox benoxacor B-170 imazapicbenoxacor B-171 imazapyr benoxacor B-172 imazaquin benoxacor B-173imazethapyr benoxacor B-174 imazosulfuron benoxacor B-175iodosulfuron-methyl-sodium benoxacor B-176 mesosulfuron benoxacor B-177nicosulfuron benoxacor B-178 penoxsulam benoxacor B-179propoxycarbazone-sodium benoxacor B-180 pyrazosulfuron-ethyl benoxacorB-181 pyroxsulam benoxacor B-182 rimsulfuron benoxacor B-183sulfosulfuron benoxacor B-184 thiencarbazone-methyl benoxacor B-185tritosulfuron benoxacor B-186 2,4-D and its salts and esters benoxacorB-187 aminopyralid and its salts and esters benoxacor B-188 clopyralidand its salts and esters benoxacor B-189 dicamba and its salts andesters benoxacor B-190 fluroxypyr-meptyl benoxacor B-191 quincloracbenoxacor B-192 quinmerac benoxacor B-193 H-9 benoxacor B-194diflufenzopyr benoxacor B-195 diflufenzopyr-sodium benoxacor B-196clomazone benoxacor B-197 diflufenican benoxacor B-198 fluorochloridonebenoxacor B-199 isoxaflutol benoxacor B-200 mesotrione benoxacor B-201picolinafen benoxacor B-202 sulcotrione benoxacor B-203 tefuryltrionebenoxacor B-204 tembotrione benoxacor B-205 topramezone benoxacor B-206H-7 benoxacor B-207 atrazine benoxacor B-208 diuron benoxacor B-209fluometuron benoxacor B-210 hexazinone benoxacor B-211 isoproturonbenoxacor B-212 metribuzin benoxacor B-213 propanil benoxacor B-214terbuthylazin benoxacor B-215 paraquat dichloride benoxacor B-216flumioxazin benoxacor B-217 oxyfluorfen benoxacor B-218 sulfentrazonebenoxacor B-219 H-1 benoxacor B-220 H-2 benoxacor B-221 glyphosatebenoxacor B-222 glyphosate-isopropylammonium benoxacor B-223glyphosate-trimesium (sulfosate) benoxacor B-224 glufosinate benoxacorB-225 glufosinate-ammonium benoxacor B-226 pendimethalin benoxacor B-227trifluralin benoxacor B-228 acetochlor benoxacor B-229 cafenstrolebenoxacor B-230 dimethenamid-P benoxacor B-231 fentrazamide benoxacorB-232 flufenacet benoxacor B-233 mefenacet benoxacor B-234 metazachlorbenoxacor B-235 metolachlor-S benoxacor B-236 pyroxasulfone benoxacorB-237 isoxaben benoxacor B-238 dymron benoxacor B-239 indanofanbenoxacor B-240 oxaziclomefone benoxacor B-241 triaziflam benoxacorB-242 atrazine + H-1 benoxacor B-243 atrazine + glyphosate benoxacorB-244 atrazine + mesotrione benoxacor B-245 atrazine + nicosulfuronbenoxacor B-246 atrazine + tembotrione benoxacor B-247 atrazine +topramezone benoxacor B-248 clomazone + glyphosate benoxacor B-249diflufenican + clodinafop-propargyl benoxacor B-250 diflufenican +fenoxaprop-P-ethyl benoxacor B-251 diflufenican +flupyrsulfuron-methyl-sodium benoxacor B-252 diflufenican + glyphosatebenoxacor B-253 diflufenican + mesosulfuron-methyl benoxacor B-254diflufenican + pinoxaden benoxacor B-255 diflufenican + pyroxsulambenoxacor B-256 flumetsulam + glyphosate benoxacor B-257 flumioxazin +glyphosate benoxacor B-258 imazapic + glyphosate benoxacor B-259imazethapyr + glyphosate benoxacor B-260 isoxaflutol + H-1 benoxacorB-261 isoxaflutol + glyphosate benoxacor B-262 metazachlor + H-1benoxacor B-263 metazachlor + glyphosate benoxacor B-264 metazachlor +mesotrione benoxacor B-265 metazachlor + nicosulfuron benoxacor B-266metazachlor + terbuthylazin benoxacor B-267 metazachlor + topramezonebenoxacor B-268 metribuzin + glyphosate benoxacor B-269 pendimethalin +H-1 benoxacor B-270 pendimethalin + clodinafop-propargyl benoxacor B-271pendimethalin + fenoxaprop-P-ethyl benoxacor B-272 pendimethalin +flupyrsulfuron-methyl-sodium benoxacor B-273 pendimethalin + glyphosatebenoxacor B-274 pendimethalin + mesosulfuron-methyl benoxacor B-275pendimethalin + mesotrionee benoxacor B-276 pendimethalin + nicosulfuronbenoxacor B-277 pendimethalin + pinoxaden benoxacor B-278pendimethalin + pyroxsulam benoxacor B-279 pendimethalin + tembotrionebenoxacor B-280 pendimethalin + topramezone benoxacor B-281pyroxasulfone + tembotrione benoxacor B-282 pyroxasulfone + topramezonebenoxacor B-283 sulfentrazone + glyphosate benoxacor B-284terbuthylazin + H-1 benoxacor B-285 terbuthylazin + foramsulfuronbenoxacor B-286 terbuthylazin + glyphosate benoxacor B-287terbuthylazin + mesotrione benoxacor B-288 terbuthylazin + nicosulfuronbenoxacor B-289 terbuthylazin + tembotrione benoxacor B-290terbuthylazin + topramezone benoxacor B-291 trifluralin + glyphosatebenoxacor B-292 clodinafop-propargyl cloquintocet B-293 cycloxydimcloquintocet B-294 cyhalofop-butyl cloquintocet B-295 fenoxaprop-P-ethylcloquintocet B-296 pinoxaden cloquintocet B-297 profoxydim cloquintocetB-298 tepraloxydim cloquintocet B-299 tralkoxydim cloquintocet B-300esprocarb cloquintocet B-301 prosulfocarb cloquintocet B-302 thiobencarbcloquintocet B-303 triallate cloquintocet B-304 bensulfuron-methylcloquintocet B-305 bispyribac-sodium cloquintocet B-306 cyclosulfamuroncloquintocet B-307 flumetsulam cloquintocet B-308flupyrsulfuron-methyl-sodium cloquintocet B-309 foramsulfuroncloquintocet B-310 imazamox cloquintocet B-311 imazapic cloquintocetB-312 imazapyr cloquintocet B-313 imazaquin cloquintocet B-314imazethapyr cloquintocet B-315 imazosulfuron cloquintocet B-316iodosulfuron-methyl-sodium cloquintocet B-317 mesosulfuron cloquintocetB-318 nicosulfuron cloquintocet B-319 penoxsulam cloquintocet B-320propoxycarbazone-sodium cloquintocet B-321 pyrazosulfuron-ethylcloquintocet B-322 pyroxsulam cloquintocet B-323 rimsulfuroncloquintocet B-324 sulfosulfuron cloquintocet B-325thiencarbazone-methyl cloquintocet B-326 tritosulfuron cloquintocetB-327 2,4-D and its salts and esters cloquintocet B-328 aminopyralid andits salts and esters cloquintocet B-329 clopyralid and its salts andesters cloquintocet B-330 dicamba and its salts and esters cloquintocetB-331 fluroxypyr-meptyl cloquintocet B-332 quinclorac cloquintocet B-333quinmerac cloquintocet B-334 H-9 cloquintocet B-335 diflufenzopyrcloquintocet B-336 diflufenzopyr-sodium cloquintocet B-337 clomazonecloquintocet B-338 diflufenican cloquintocet B-339 fluorochloridonecloquintocet B-340 isoxaflutol cloquintocet B-341 mesotrionecloquintocet B-342 picolinafen cloquintocet B-343 sulcotrionecloquintocet B-344 tefuryltrione cloquintocet B-345 tembotrionecloquintocet B-346 topramezone cloquintocet B-347 H-7 cloquintocet B-348atrazine cloquintocet B-349 diuron cloquintocet B-350 fluometuroncloquintocet B-351 hexazinone cloquintocet B-352 isoproturoncloquintocet B-353 metribuzin cloquintocet B-354 propanil cloquintocetB-355 terbuthylazin cloquintocet B-356 paraquat dichloride cloquintocetB-357 flumioxazin cloquintocet B-358 oxyfluorfen cloquintocet B-359sulfentrazone cloquintocet B-360 H-1 cloquintocet B-361 H-2 cloquintocetB-362 glyphosate cloquintocet B-363 glyphosate-isopropylammoniumcloquintocet B-364 glyphosate-trimesium (sulfosate) cloquintocet B-365glufosinate cloquintocet B-366 glufosinate-ammonium cloquintocet B-367pendimethalin cloquintocet B-368 trifluralin cloquintocet B-369acetochlor cloquintocet B-370 cafenstrole cloquintocet B-371dimethenamid-P cloquintocet B-372 fentrazamide cloquintocet B-373flufenacet cloquintocet B-374 mefenacet cloquintocet B-375 metazachlorcloquintocet B-376 metolachlor-S cloquintocet B-377 pyroxasulfonecloquintocet B-378 isoxaben cloquintocet B-379 dymron cloquintocet B-380indanofan cloquintocet B-381 oxaziclomefone cloquintocet B-382triaziflam cloquintocet B-383 atrazine + H-1 cloquintocet B-384atrazine + glyphosate cloquintocet B-385 atrazine + mesotrionecloquintocet B-386 atrazine + nicosulfuron cloquintocet B-387 atrazine +tembotrione cloquintocet B-388 atrazine + topramezone cloquintocet B-389clomazone + glyphosate cloquintocet B-390 diflufenican +clodinafop-propargyl cloquintocet B-391 diflufenican +fenoxaprop-p-ethyl cloquintocet B-392 diflufenican +flupyrsulfuron-methyl-sodium cloquintocet B-393 diflufenican +glyphosate cloquintocet B-394 diflufenican + mesosulfuron-methylcloquintocet B-395 diflufenican + pinoxaden cloquintocet B-396diflufenican + pyroxsulam cloquintocet B-397 flumetsulam + glyphosatecloquintocet B-398 flumioxazin + glyphosate cloquintocet B-399imazapic + glyphosate cloquintocet B-400 imazethapyr + glyphosatecloquintocet B-401 isoxaflutol + H-1 cloquintocet B-402 isoxaflutol +glyphosate cloquintocet B-403 metazachlor + H-1 cloquintocet B-404metazachlor + glyphosate cloquintocet B-405 metazachlor + mesotrionecloquintocet B-406 metazachlor + nicosulfuron cloquintocet B-407metazachlor + terbuthylazin cloquintocet B-408 metazachlor + topramezonecloquintocet B-409 metribuzin + glyphosate cloquintocet B-410pendimethalin + H-1 cloquintocet B-411 pendimethalin +clodinafop-propargyl cloquintocet B-412 pendimethalin +fenoxaprop-P-ethyl cloquintocet B-413 pendimethalin +flupyrsulfuron-methyl-sodium cloquintocet B-414 pendimethalin +glyphosate cloquintocet B-415 pendimethalin + mesosulfuron-methylcloquintocet B-416 pendimethalin + mesotrione cloquintocet B-417pendimethalin + nicosulfuron cloquintocet B-418 pendimethalin +pinoxaden cloquintocet B-419 pendimethalin + pyroxsulam cloquintocetB-420 pendimethalin + tembotrione cloquintocet B-421 pendimethalin +topramezone cloquintocet B-422 pyroxasulfone + tembotrione cloquintocetB-423 pyroxasulfone + topramezone cloquintocet B-424 sulfentrazone +glyphosate cloquintocet B-425 terbuthylazin + H-1 cloquintocet B-426terbuthylazin + foramsulfuron cloquintocet B-427 terbuthylazin +glyphosate cloquintocet B-428 terbuthylazin + mesotrione cloquintocetB-429 terbuthylazin + nicosulfuron cloquintocet B-430 terbuthylazin +tembotrione cloquintocet B-431 terbuthylazin + topramezone cloquintocetB-432 trifluralin + glyphosate cloquintocet B-433 clodinafop-propargyldichlormid B-434 cycloxydim dichlormid B-435 cyhalofop-butyl dichlormidB-436 fenoxaprop-P-ethyl dichlormid B-437 pinoxaden dichlormid B-438profoxydim dichlormid B-439 tepraloxydim dichlormid B-440 tralkoxydimdichlormid B-441 esprocarb dichlormid B-442 prosulfocarb dichlormidB-443 thiobencarb dichlormid B-444 triallate dichlormid B-445bensulfuron-methyl dichlormid B-446 bispyribac-sodium dichlormid B-447cyclosulfamuron dichlormid B-448 flumetsulam dichlormid B-449flupyrsulfuron-methyl-sodium dichlormid B-450 foramsulfuron dichlormidB-451 imazamox dichlormid B-452 imazapic dichlormid B-453 imazapyrdichlormid B-454 imazaquin dichlormid B-455 imazethapyr dichlormid B-456imazosulfuron dichlormid B-457 iodosulfuron-methyl-sodium dichlormidB-458 mesosulfuron dichlormid B-459 nicosulfuron dichlormid B-460penoxsulam dichlormid B-461 propoxycarbazone-sodium dichlormid B-462pyrazosulfuron-ethyl dichlormid B-463 pyroxsulam dichlormid B-464rimsulfuron dichlormid B-465 sulfosulfuron dichlormid B-466thiencarbazone-methyl dichlormid B-467 tritosulfuron dichlormid B-4682,4-D and its salts and esters dichlormid B-469 aminopyralid and itssalts and esters dichlormid B-470 clopyralid and its salts and estersdichlormid B-471 dicamba and its salts and esters dichlormid B-472fluroxypyr-meptyl dichlormid B-473 quinclorac dichlormid B-474 quinmeracdichlormid B-475 H-9 dichlormid B-476 diflufenzopyr dichlormid B-477diflufenzopyr-sodium dichlormid B-478 clomazone dichlormid B-479diflufenican dichlormid B-480 fluorochloridone dichlormid B-481isoxaflutol dichlormid B-482 mesotrione dichlormid B-483 picolinafendichlormid B-484 sulcotrione dichlormid B-485 tefuryltrione dichlormidB-486 tembotrione dichlormid B-487 topramezone dichlormid B-488 H-7dichlormid B-489 atrazine dichlormid B-490 diuron dichlormid B-491fluometuron dichlormid B-492 hexazinone dichlormid B-493 isoproturondichlormid B-494 metribuzin dichlormid B-495 propanil dichlormid B-496terbuthylazin dichlormid B-497 paraquat dichloride dichlormid B-498flumioxazin dichlormid B-499 oxyfluorfen dichlormid B-500 sulfentrazonedichlormid B-501 H-1 dichlormid B-502 H-2 dichlormid B-503 glyphosatedichlormid B-504 glyphosate-isopropylammonium dichlormid B-505glyphosate-trimesium (sulfosate) dichlormid B-506 glufosinate dichlormidB-507 glufosinate-ammonium dichlormid B-508 pendimethalin dichlormidB-509 trifluralin dichlormid B-510 acetochlor dichlormid B-511cafenstrole dichlormid B-512 dimethenamid-P dichlormid B-513fentrazamide dichlormid B-514 flufenacet dichlormid B-515 mefenacetdichlormid B-516 metazachlor dichlormid B-517 metolachlor-S dichlormidB-518 pyroxasulfone dichlormid B-519 isoxaben dichlormid B-520 dymrondichlormid B-521 indanofan dichlormid B-522 oxaziclomefone dichlormidB-523 triaziflam dichlormid B-524 atrazine + H-1 dichlormid B-525atrazine + glyphosate dichlormid B-526 atrazine + mesotrione dichlormidB-527 atrazine + nicosulfuron dichlormid B-528 atrazine + tembotrionedichlormid B-529 atrazine + topramezone dichlormid B-530 clomazone +glyphosate dichlormid B-531 diflufenican + clodinafop-propargyldichlormid B-532 diflufenican + fenoxaprop-P-ethyl dichlormid B-533diflufenican + flupyrsulfuron-methyl-sodium dichlormid B-534diflufenican + glyphosate dichlormid B-535 diflufenican +mesosulfuron-methyl dichlormid B-536 diflufenican + pinoxaden dichlormidB-537 diflufenican + pyroxsulam dichlormid B-538 flumetsulam +glyphosate dichlormid B-539 flumioxazin + glyphosate dichlormid B-540imazapic + glyphosate dichlormid B-541 imazethapyr + glyphosatedichlormid B-542 isoxaflutol + H-1 dichlormid B-543 isoxaflutol +glyphosate dichlormid B-544 metazachlor + H-1 dichlormid B-545metazachlor + glyphosate dichlormid B-546 metazachlor + mesotrionedichlormid B-547 metazachlor + nicosulfuron dichlormid B-548metazachlor + terbuthylazin dichlormid B-549 metazachlor + topramezonedichlormid B-550 metribuzin + glyphosate dichlormid B-551pendimethalin + H-1 dichlormid B-552 pendimethalin +clodinafop-propargyl dichlormid B-553 pendimethalin + fenoxaprop-P-ethyldichlormid B-554 pendimethalin + flupyrsulfuron-methyl-sodium dichlormidB-555 pendimethalin + glyphosate dichlormid B-556 pendimethalin +mesosulfuron-methyl dichlormid B-557 pendimethalin + mesotrionedichlormid B-558 pendimethalin + nicosulfuron dichlormid B-559pendimethalin + pinoxaden dichlormid B-560 pendimethalin + pyroxsulamdichlormid B-561 pendimethalin + tembotrione dichlormid B-562pendimethalin + topramezone dichlormid B-563 pyroxasulfone + tembotrionedichlormid B-564 pyroxasulfone + topramezone dichlormid B-565sulfentrazone + glyphosate dichlormid B-566 ferbuthylazin + H-1dichlormid B-567 terbuthylazin + foramsulfuron dichlormid B-568terbuthylazin + glyphosate dichlormid B-569 terbuthylazin + mesotrionedichlormid B-570 terbuthylazin + nicosulfuron dichlormid B-571terbuthylazin + tembotrione dichlormid B-572 terbuthylazin + topramezonedichlormid B-573 trifluralin + glyphosate dichlormid B-574clodinafop-propargyl fenchlorazole B-575 cycloxydim fenchlorazole B-576cyhalofop-butyl fenchlorazole B-577 fenoxaprop-P-ethyl fenchlorazoleB-578 pinoxaden fenchlorazole B-579 profoxydim fenchlorazole B-580tepraloxydim fenchlorazole B-581 tralkoxydim fenchlorazole B-582esprocarb fenchlorazole B-583 prosulfocarb fenchlorazole B-584thiobencarb fenchlorazole B-585 triallate fenchlorazole B-586bensulfuron-methyl fenchlorazole B-587 bispyribac-sodium fenchlorazoleB-588 cyclosulfamuron fenchlorazole B-589 flumetsulam fenchlorazoleB-590 flupyrsulfuron-methyl-sodium fenchlorazole B-591 foramsulfuronfenchlorazole B-592 imazamox fenchlorazole B-593 imazapic fenchlorazoleB-594 imazapyr fenchlorazole B-595 imazaquin fenchlorazole B-596imazethapyr fenchlorazole B-597 imazosulfuron fenchlorazole B-598iodosulfuron-methyl-sodium fenchlorazole B-599 mesosulfuronfenchlorazole B-600 nicosulfuron fenchlorazole B-601 penoxsulamfenchlorazole B-602 propoxycarbazone-sodium fenchlorazole B-603pyrazosulfuron-ethyl fenchlorazole B-604 pyroxsulam fenchlorazole B-605rimsulfuron fenchlorazole B-606 sulfosulfuron fenchlorazole B-607thiencarbazone-methyl fenchlorazole B-608 tritosulfuron fenchlorazoleB-609 2,4-D and its salts and esters fenchlorazole B-610 aminopyralidand its salts and esters fenchlorazole B-611 clopyralid and its saltsand esters fenchlorazole B-612 dicamba and its salts and estersfenchlorazole B-613 fluroxypyr-meptyl fenchlorazole B-614 quincloracfenchlorazole B-615 quinmerac fenchlorazole B-616 H-9 fenchlorazoleB-617 diflufenzopyr fenchlorazole B-618 diflufenzopyr-sodiumfenchlorazole B-619 clomazone fenchlorazole B-620 diflufenicanfenchlorazole B-621 fluorochloridone fenchlorazole B-622 isoxaflutolfenchlorazole B-623 mesotrione fenchlorazole B-624 picolinafenfenchlorazole B-625 sulcotrione fenchlorazole B-626 tefuryltrionefenchlorazole B-627 tembotrione fenchlorazole B-628 topramezonefenchlorazole B-629 H-7 fenchlorazole B-630 atrazine fenchlorazole B-631diuron fenchlorazole B-632 fluometuron fenchlorazole B-633 hexazinonefenchlorazole B-634 isoproturon fenchlorazole B-635 metribuzinfenchlorazole B-636 propanil fenchlorazole B-637 terbuthylazinfenchlorazole B-638 paraquat dichloride fenchlorazole B-639 flumioxazinfenchlorazole B-640 oxyfluorfen fenchlorazole B-641 sulfentrazonefenchlorazole B-642 H-1 fenchlorazole B-643 H-2 fenchlorazole B-644glyphosate fenchlorazole B-645 glyphosate-isopropylammoniumfenchlorazole B-646 glyphosate-trimesium (sulfosate) fenchlorazole B-647glufosinate fenchlorazole B-648 glufosinate-ammonium fenchlorazole B-649pendimethalin fenchlorazole B-650 trifluralin fenchlorazole B-651acetochlor fenchlorazole B-652 cafenstrole fenchlorazole B-653dimethenamid-P fenchlorazole B-654 fentrazamide fenchlorazole B-655flufenacet fenchlorazole B-656 mefenacet fenchlorazole B-657 metazachlorfenchlorazole B-658 metolachlor-S fenchlorazole B-659 pyroxasulfonefenchlorazole B-660 isoxaben fenchlorazole B-661 dymron fenchlorazoleB-662 indanofan fenchlorazole B-663 oxaziclomefone fenchlorazole B-664friaziflam fenchlorazole B-665 atrazine + H-1 fenchlorazole B-666atrazine + glyphosate fenchlorazole B-667 atrazine + mesotrionefenchlorazole B-668 atrazine + nicosulfuron fenchlorazole B-669atrazine + tembotrione fenchlorazole B-670 atrazine + topramezonefenchlorazole B-671 clomazone + glyphosate fenchlorazole B-672diflufenican + clodinafop-propargyl fenchlorazole B-673 diflufenican +fenoxaprop-P-ethyl fenchlorazole B-674 diflufenican +flupyrsulfuron-methyl-sodium fenchlorazole B-675 diflufenican +glyphosate fenchlorazole B-676 diflufenican + mesosulfuron-methylfenchlorazole B-677 diflufenican + pinoxaden fenchlorazole B-678diflufenican + pyroxsulam fenchlorazole B-679 flumetsulam + glyphosatefenchlorazole B-680 flumioxazin + glyphosate fenchlorazole B-681imazapic + glyphosate fenchlorazole B-682 imazethapyr + glyphosatefenchlorazole B-683 isoxaflutol + H-1 fenchlorazole B-684 isoxaflutol +glyphosate fenchlorazole B-685 metazachlor + H-1 fenchlorazole B-686metazachlor + glyphosate fenchlorazole B-687 metazachlor + mesotrionefenchlorazole B-688 metazachlor + nicosulfuron fenchlorazole B-689metazachlor + terbuthylazin fenchlorazole B-690 metazachlor +topramezone fenchlorazole B-691 metribuzin + glyphosate fenchlorazoleB-692 pendimethalin + H-1 fenchlorazole B-693 pendimethalin +clodinafop-propargyl fenchlorazole B-694 pendimethalin +fenoxaprop-P-ethyl fenchlorazole B-695 pendimethalin +flupyrsulfuron-methyl-sodium fenchlorazole B-696 pendimethalin +glyphosate fenchlorazole B-697 pendimethalin + mesosulfuron-methylfenchlorazole B-698 pendimethalin + mesotrione fenchlorazole B-699pendimethalin + nicosulfuron fenchlorazole B-700 pendimethalin +pinoxaden fenchlorazole B-701 pendimethalin + pyroxsulam fenchlorazoleB-702 pendimethalin + tembotrione fenchlorazole B-703 pendimethalin +topramezone fenchlorazole B-704 pyroxasulfone + tembotrionefenchlorazole B-705 pyroxasulfone + topramezone fenchlorazole B-706sulfentrazone + glyphosate fenchlorazole B-707 terbuthylazin + H-1fenchlorazole B-708 terbuthylazin + foramsulfuron fenchlorazole B-709terbuthylazin + glyphosate fenchlorazole B-710 terbuthylazin +mesotrione fenchlorazole B-711 terbuthylazin + nicosulfuronfenchlorazole B-712 terbuthylazin + tembotrione fenchlorazole B-713terbuthylazin + topramezone fenchlorazole B-714 trifluralin + glyphosatefenchlorazole B-715 clodinafop-propargyl isoxadifen B-716 cycloxydimisoxadifen B-717 cyhalofop-butyl isoxadifen B-718 fenoxaprop-P-ethylisoxadifen B-719 pinoxaden isoxadifen B-720 profoxydim isoxadifen B-721tepraloxydim isoxadifen B-722 tralkoxydim isoxadifen B-723 esprocarbisoxadifen B-724 prosulfocarb isoxadifen B-725 thiobencarb isoxadifenB-726 triallate isoxadifen B-727 bensulfuron-methyl isoxadifen B-728bispyribac-sodium isoxadifen B-729 cyclosulfamuron isoxadifen B-730flumetsulam isoxadifen B-731 flupyrsulfuron-methyl-sodium isoxadifenB-732 foramsulfuron isoxadifen B-733 imazamox isoxadifen B-734 imazapicisoxadifen B-735 imazapyr isoxadifen B-736 imazaquin isoxadifen B-737imazethapyr isoxadifen B-738 imazosulfuron isoxadifen B-739iodosulfuron-methyl-sodium isoxadifen B-740 mesosulfuron isoxadifenB-741 nicosulfuron isoxadifen B-742 penoxsulam isoxadifen B-743propoxycarbazone-sodium isoxadifen B-744 pyrazosulfuron-ethyl isoxadifenB-745 pyroxsulam isoxadifen B-746 rimsulfuron isoxadifen B-747sulfosulfuron isoxadifen B-748 thiencarbazone-methyl isoxadifen B-749tritosulfuron isoxadifen B-750 2,4-D and its salts and esters isoxadifenB-751 aminopyralid and its salts and esters isoxadifen B-752 clopyralidand its salts and esters isoxadifen B-753 dicamba and its salts andesters isoxadifen B-754 fluroxypyr-meptyl isoxadifen B-755 quincloracisoxadifen B-756 quinmerac isoxadifen B-757 H-9 isoxadifen B-758diflufenzopyr isoxadifen B-759 diflufenzopyr-sodium isoxadifen B-760clomazone isoxadifen B-761 diflufenican isoxadifen B-762fluorochloridone isoxadifen B-763 isoxaflutol isoxadifen B-764mesotrione isoxadifen B-765 picolinafen isoxadifen B-766 sulcotrioneisoxadifen B-767 tefuryltrione isoxadifen B-768 tembotrione isoxadifenB-769 topramezone isoxadifen B-770 H-7 isoxadifen B-771 atrazineisoxadifen B-772 diuron isoxadifen B-773 fluometuron isoxadifen B-774hexazinone isoxadifen B-775 isoproturon isoxadifen B-776 metribuzinisoxadifen B-777 propanil isoxadifen B-778 terbuthylazin isoxadifenB-779 paraquat dichloride isoxadifen B-780 flumioxazin isoxadifen B-781oxyfluorfen isoxadifen B-782 sulfentrazone isoxadifen B-783 H-1isoxadifen B-784 H-2 isoxadifen B-785 glyphosate isoxadifen B-786glyphosate-isopropylammonium isoxadifen B-787 glyphosate-trimesium(sulfosate) isoxadifen B-788 glufosinate isoxadifen B-789glufosinate-ammonium isoxadifen B-790 pendimethalin isoxadifen B-791trifluralin isoxadifen B-792 acetochlor isoxadifen B-793 cafenstroleisoxadifen B-794 dimethenamid-P isoxadifen B-795 fentrazamide isoxadifenB-796 flufenacet isoxadifen B-797 mefenacet isoxadifen B-798 metazachlorisoxadifen B-799 metolachlor-S isoxadifen B-800 pyroxasulfone isoxadifenB-801 isoxaben isoxadifen B-802 dymron isoxadifen B-803 indanofanisoxadifen B-804 oxaziclomefone isoxadifen B-805 triaziflam isoxadifenB-806 atrazine + H-1 isoxadifen B-807 atrazine + glyphosate isoxadifenB-808 atrazine + mesotrione isoxadifen B-809 atrazine + nicosulfuronisoxadifen B-810 atrazine + tembotrione isoxadifen B-811 atrazine +topramezone isoxadifen B-812 clomazone + glyphosate isoxadifen B-813diflufenican + clodinafop-propargyl isoxadifen B-814 diflufenican +fenoxaprop-P-ethyl isoxadifen B-815 diflufenican +flupyrsulfuron-methyl-sodium isoxadifen B-816 diflufenican + glyphosateisoxadifen B-817 diflufenican + mesosulfuron-methyl isoxadifen B-818diflufenican + pinoxaden isoxadifen B-819 diflufenican + pyroxsulamisoxadifen B-820 flumetsulam + glyphosate isoxadifen B-821 flumioxazin +glyphosate isoxadifen B-822 imazapic + glyphosate isoxadifen B-823imazethapyr + glyphosate isoxadifen B-824 isoxaflutol + H-1 isoxadifenB-825 isoxaflutol + glyphosate isoxadifen B-826 metazachlor + H-1isoxadifen B-827 metazachlor + glyphosate isoxadifen B-828 metazachlor +mesotrione isoxadifen B-829 metazachlor + nicosulfuron isoxadifen B-830metazachlor + terbuthylazin isoxadifen B-831 metazachlor + topramezoneisoxadifen B-832 metribuzin + glyphosate isoxadifen B-833pendimethalin + H-1 isoxadifen B-834 pendimethalin +clodinafop-propargyl isoxadifen B-835 pendimethalin + fenoxaprop-P-ethylisoxadifen B-836 pendimethalin + flupyrsulfuron-methyl-sodium isoxadifenB-837 pendimethalin + glyphosate isoxadifen B-838 pendimethalin +mesosulfuron-methyl isoxadifen B-839 pendimethalin + mesotrioneisoxadifen B-840 pendimethalin + nicosulfuron isoxadifen B-841pendimethalin + pinoxaden isoxadifen B-842 pendimethalin + pyroxsulamisoxadifen B-843 pendimethalin + tembotrione isoxadifen B-844pendimethalin + topramezone isoxadifen B-845 pyroxasulfone + tembotrioneisoxadifen B-846 pyroxasulfone + topramezone isoxadifen B-847sulfentrazone + glyphosate isoxadifen B-848 terbuthylazin + H-1isoxadifen B-849 terbuthylazin + foramsulfuron isoxadifen B-850terbuthylazin + glyphosate isoxadifen B-851 terbuthylazin + mesotrioneisoxadifen B-852 terbuthylazin + nicosulfuron isoxadifen B-853terbuthylazin + tembotrione isoxadifen B-854 terbuthylazin + topramezoneisoxadifen B-855 trifluralin + glyphosate isoxadifen B-856clodinafop-propargyl mefenpyr B-857 cycloxydim mefenpyr B-858cyhalofop-butyl mefenpyr B-859 fenoxaprop-P-ethyl mefenpyr B-860pinoxaden mefenpyr B-861 profoxydim mefenpyr B-862 tepraloxydim mefenpyrB-863 tralkoxydim mefenpyr B-864 esprocarb mefenpyr B-865 prosulfocarbmefenpyr B-866 thiobencarb mefenpyr B-867 triallate mefenpyr B-868bensulfuron-methyl mefenpyr B-869 bispyribac-sodium mefenpyr B-870cyclosulfamuron mefenpyr B-871 flumetsulam mefenpyr B-872flupyrsulfuron-methyl-sodium mefenpyr B-873 foramsulfuron mefenpyr B-874imazamox mefenpyr B-875 imazapic mefenpyr B-876 imazapyr mefenpyr B-877imazaquin mefenpyr B-878 imazethapyr mefenpyr B-879 imazosulfuronmefenpyr B-880 iodosulfuron-methyl-sodium mefenpyr B-881 mesosulfuronmefenpyr B-882 nicosulfuron mefenpyr B-883 penoxsulam mefenpyr B-884propoxycarbazone-sodium mefenpyr B-885 pyrazosulfuron-ethyl mefenpyrB-886 pyroxsulam mefenpyr B-887 rimsulfuron mefenpyr B-888 sulfosulfuronmefenpyr B-889 thiencarbazone-methyl mefenpyr B-890 tritosulfuronmefenpyr B-891 2,4-D and its salts and esters mefenpyr B-892aminopyralid and its salts and esters mefenpyr B-893 clopyralid and itssalts and esters mefenpyr B-894 dicamba and its salts and estersmefenpyr B-895 fluroxypyr-meptyl mefenpyr B-896 quinclorac mefenpyrB-897 quinmerac mefenpyr B-898 H-9 mefenpyr B-899 diflufenzopyr mefenpyrB-900 diflufenzopyr-sodium mefenpyr B-901 clomazone mefenpyr B-902diflufenican mefenpyr B-903 fluorochloridone mefenpyr B-904 isoxaflutolmefenpyr B-905 mesotrione mefenpyr B-906 picolinafen mefenpyr B-907sulcotrione mefenpyr B-908 tefuryltrione mefenpyr B-909 tembotrionemefenpyr B-910 topramezone mefenpyr B-911 H-7 mefenpyr B-912 atrazinemefenpyr B-913 diuron mefenpyr B-914 fluometuron mefenpyr B-915hexazinone mefenpyr B-916 isoproturon mefenpyr B-917 metribuzin mefenpyrB-918 propanil mefenpyr B-919 terbuthylazin mefenpyr B-920 paraquatdichloride mefenpyr B-921 flumioxazin mefenpyr B-922 oxyfluorfenmefenpyr B-923 sulfentrazone mefenpyr B-924 H-1 mefenpyr B-925 H-2mefenpyr B-926 glyphosate mefenpyr B-927 glyphosate-isopropylammoniummefenpyr B-928 glyphosate-trimesium (sulfosate) mefenpyr B-929glufosinate mefenpyr B-930 glufosinate-ammonium mefenpyr B-931pendimethalin mefenpyr B-932 trifluralin mefenpyr B-933 acetochlormefenpyr B-934 cafenstrole mefenpyr B-935 dimethenamid-p mefenpyr B-936fentrazamide mefenpyr B-937 flufenacet mefenpyr B-938 mefenacet mefenpyrB-939 metazachlor mefenpyr B-940 metolachlor-S mefenpyr B-941pyroxasulfone mefenpyr B-942 isoxaben mefenpyr B-943 dymron mefenpyrB-944 indanofan mefenpyr B-945 oxaziclomefone mefenpyr B-946 triaziflammefenpyr B-947 atrazine + H-1 mefenpyr B-948 atrazine + glyphosatemefenpyr B-949 atrazine + mesotrione mefenpyr B-950 atrazine +nicosulfuron mefenpyr B-951 atrazine + tembotrione mefenpyr B-952atrazine + topramezone mefenpyr B-953 clomazone + glyphosate mefenpyrB-954 diflufenican + clodinafop-propargyl mefenpyr B-955 diflufenican +fenoxaprop-P-ethyl mefenpyr B-956 diflufenican +flupyrsulfuron-methyl-sodium mefenpyr B-957 diflufenican + glyphosatemefenpyr B-958 diflufenican + mesosulfuron-methyl mefenpyr B-959diflufenican + pinoxaden mefenpyr B-960 diflufenican + pyroxsulammefenpyr B-961 flumetsulam + glyphosate mefenpyr B-962 flumioxazin +glyphosate mefenpyr B-963 imazapic + glyphosate mefenpyr B-964imazethapyr + glyphosate mefenpyr B-965 isoxaflutol + H-1 mefenpyr B-966isoxaflutol + glyphosate mefenpyr B-967 metazachlor + H-1 mefenpyr B-968metazachlor + glyphosate mefenpyr B-969 metazachlor + mesotrionemefenpyr B-970 metazachlor + nicosulfuron mefenpyr B-971 metazachlor +terbuthylazin mefenpyr B-972 metazachlor + topramezone mefenpyr B-973metribuzin + glyphosate mefenpyr B-974 pendimethalin + H-1 mefenpyrB-975 pendimethalin + clodinafop-propargyl mefenpyr B-976pendimethalin + fenoxaprop-P-ethyl mefenpyr B-977 pendimethalin +flupyrsulfuron-methyl-sodium mefenpyr B-978 pendimethalin + glyphosatemefenpyr B-979 pendimethalin + mesosulfuron-methyl mefenpyr B-980pendimethalin + mesotrione mefenpyr B-981 pendimethalin + nicosulfuronmefenpyr B-982 pendimethalin + pinoxaden mefenpyr B-983 pendimethalin +pyroxsulam mefenpyr B-984 pendimethalin + tembotrione mefenpyr B-985pendimethalin + topramezone mefenpyr B-986 pyroxasulfone + tembotrionemefenpyr B-987 pyroxasulfone + topramezone mefenpyr B-988sulfentrazone + glyphosate mefenpyr B-989 terbuthylazin + H-1 mefenpyrB-990 terbuthylazin + foramsulfuron mefenpyr B-991 terbuthylazin +glyphosate mefenpyr B-992 terbuthylazin + mesotrione mefenpyr B-993terbuthylazin + nicosulfuron mefenpyr B-994 terbuthylazin + tembotrionemefenpyr B-995 terbuthylazin + topramezone mefenpyr B-996 trifluralin +glyphosate mefenpyr B-997 clodinafop-propargyl H-12 B-998 cycloxydimH-12 B-999 cyhalofop-butyl H-12 B-1000 fenoxaprop-P-ethyl H-12 B-1001pinoxaden H-12 B-1002 profoxydim H-12 B-1003 tepraloxydim H-12 B-1004tralkoxydim H-12 B-1005 esprocarb H-12 B-1006 prosulfocarb H-12 B-1007thiobencarb H-12 B-1008 triallate H-12 B-1009 bensulfuron-methyl H-12B-1010 bispyribac-sodium H-12 B-1011 cyclosulfamuron H-12 B-1012flumetsulam H-12 B-1013 flupyrsulfuron-methyl-sodium H-12 B-1014foramsulfuron H-12 B-1015 imazamox H-12 B-1016 imazapic H-12 B-1017imazapyr H-12 B-1018 imazaquin H-12 B-1019 imazethapyr H-12 B-1020imazosulfuron H-12 B-1021 iodosulfuron-methyl-sodium H-12 B-1022mesosulfuron H-12 B-1023 nicosulfuron H-12 B-1024 penoxsulam H-12 B-1025propoxycarbazone-sodium H-12 B-1026 pyrazosulfuron-ethyl H-12 B-1027pyroxsulam H-12 B-1028 rimsulfuron H-12 B-1029 sulfosulfuron H-12 B-1030thiencarbazone-methyl H-12 B-1031 tritosulfuron H-12 B-1032 2,4-D andits salts and esters H-12 B-1033 aminopyralid and its salts and estersH-12 B-1034 clopyralid and its salts and esters H-12 B-1035 dicamba andits salts and esters H-12 B-1036 fluroxypyr-meptyl H-12 B-1037quinclorac H-12 B-1038 quinmerac H-12 B-1039 H-9 H-12 B-1040diflufenzopyr H-12 B-1041 diflufenzopyr-sodium H-12 B-1042 clomazoneH-12 B-1043 diflufenican H-12 B-1044 fluorochloridone H-12 B-1045isoxaflutol H-12 B-1046 mesotrione H-12 B-1047 picolinafen H-12 B-1048sulcotrione H-12 B-1049 tefuryltrione H-12 B-1050 tembotrione H-12B-1051 topramezone H-12 B-1052 H-7 H-12 B-1053 atrazine H-12 B-1054diuron H-12 B-1055 fluometuron H-12 B-1056 hexazinone H-12 B-1057isoproturon H-12 B-1058 metribuzin H-12 B-1059 propanil H-12 B-1060terbuthylazin H-12 B-1061 paraquat dichloride H-12 B-1062 flumioxazinH-12 B-1063 oxyfluorfen H-12 B-1064 sulfentrazone H-12 B-1065 H-1 H-12B-1066 H-2 H-12 B-1067 glyphosate H-12 B-1068glyphosate-isopropylammonium H-12 B-1069 glyphosate-trimesium(sulfosate) H-12 B-1070 glufosinate H-12 B-1071 glufosinate-ammoniumH-12 B-1072 pendimethalin H-12 B-1073 trifluralin H-12 B-1074 acetochlorH-12 B-1075 cafenstrole H-12 B-1076 dimethenamid-P H-12 B-1077fentrazamide H-12 B-1078 flufenacet H-12 B-1079 mefenacet H-12 B-1080metazachlor H-12 B-1081 metolachlor-S H-12 B-1082 pyroxasulfone H-12B-1083 isoxaben H-12 B-1084 dymron H-12 B-1085 indanofan H-12 B-1086oxaziclomefone H-12 B-1087 triaziflam H-12 B-1088 atrazine + H-1 H-12B-1089 atrazine + glyphosate H-12 B-1090 atrazine + mesotrione H-12B-1091 atrazine + nicosulfuron H-12 B-1092 atrazine + tembotrione H-12B-1093 atrazine + topramezone H-12 B-1094 clomazone + glyphosate H-12B-1095 diflufenican + clodinafop-propargyl H-12 B-1096 diflufenican +fenoxaprop-P-ethyl H-12 B-1097 diflufenican +flupyrsulfuron-methyl-sodium H-12 B-1098 diflufenican + glyphosate H-12B-1099 diflufenican + mesosulfuron-methyl H-12 B-1100 diflufenican +pinoxaden H-12 B-1101 diflufenican + pyroxsulam H-12 B-1102flumetsulam + glyphosate H-12 B-1103 flumioxazin + glyphosate H-12B-1104 imazapic + glyphosate H-12 B-1105 imazethapyr + glyphosate H-12B-1106 isoxaflutol + H-1 H-12 B-1107 isoxaflutol + glyphosate H-12B-1108 metazachlor + H-1 H-12 B-1109 metazachlor + glyphosate H-12B-1110 metazachlor + mesotrione H-12 B-1111 metazachlor + nicosulfuronH-12 B-1112 metazachlor + terbuthylazin H-12 B-1113 metazachlor +topramezone H-12 B-1114 metribuzin + glyphosate H-12 B-1115pendimethalin + H-1 H-12 B-1116 pendimethalin + clodinafop-propargylH-12 B-1117 pendimethalin + fenoxaprop-P-ethyl H-12 B-1118pendimethalin + flupyrsulfuron-methyl-sodium H-12 B-1119 pendimethalin +glyphosate H-12 B-1120 pendimethalin + mesosulfuron-methyl H-12 B-1121pendimethalin + mesotrionee H-12 B-1122 pendimethalin + nicosulfuronH-12 B-1123 pendimethalin + pinoxaden H-12 B-1124 pendimethalin +pyroxsulam H-12 B-1125 pendimethalin + tembotrione H-12 B-1126pendimethalin + topramezone H-12 B-1127 pyroxasulfone + tembotrione H-12B-1128 pyroxasulfone + topramezone H-12 B-1129 sulfentrazone +glyphosate H-12 B-1130 terbuthylazin + H-1 H-12 B-1131 terbuthylazin +foramsulfuron H-12 B-1132 terbuthylazin + glyphosate H-12 B-1133terbuthylazin + mesotrione H-12 B-1134 terbuthylazin + nicosulfuron H-12B-1135 terbuthylazin + tembotrione H-12 B-1136 terbuthylazin +topramezone H-12 B-1137 trifluralin + glyphosate H-12 B-1138 2-1 —B-1139 2-2 — B-1140 2-3 — B-1141 2-4 — B-1142 2-5 — B-1143 2-6 — B-11442-7 — B-1145 2-8 — B-1146 2-9 — B-1147 2-1 benoxacor B-1148 2-2benoxacor B-1149 2-3 benoxacor B-1150 2-4 benoxacor B-1151 2-5 benoxacorB-1152 2-6 benoxacor B-1153 2-7 benoxacor B-1154 2-8 benoxacor B-11552-9 benoxacor B-1156 2-1 cloquintocet B-1157 2-2 cloquintocet B-1158 2-3cloquintocet B-1159 2-4 cloquintocet B-1160 2-5 cloquintocet B-1161 2-6cloquintocet B-1162 2-7 cloquintocet B-1163 2-8 cloquintocet B-1164 2-9cloquintocet B-1165 2-1 cyprosulfamide B-1166 2-2 cyprosulfamide B-11672-3 cyprosulfamide B-1168 2-4 cyprosulfamide B-1169 2-5 cyprosulfamideB-1170 2-6 cyprosulfamide B-1171 2-7 cyprosulfamide B-1172 2-8cyprosulfamide B-1173 2-9 cyprosulfamide B-1174 2-1 dichlormid B-11752-2 dichlormid B-1176 2-3 dichlormid B-1177 2-4 dichlormid B-1178 2-5dichlormid B-1179 2-6 dichlormid B-1180 2-7 dichlormid B-1181 2-8dichlormid B-1182 2-9 dichlormid B-1183 2-1 fenchlorazole B-1184 2-2fenchlorazole B-1185 2-3 fenchlorazole B-1186 2-4 fenchlorazole B-11872-5 fenchlorazole B-1188 2-6 fenchlorazole B-1189 2-7 fenchlorazoleB-1190 2-8 fenchlorazole B-1191 2-9 fenchlorazole B-1192 2-1 isoxadifenB-1193 2-2 isoxadifen B-1194 2-3 isoxadifen B-1195 2-4 isoxadifen B-11962-5 isoxadifen B-1197 2-6 isoxadifen B-1198 2-7 isoxadifen B-1199 2-8isoxadifen B-1200 2-9 isoxadifen B-1201 2-1 mefenpyr B-1202 2-2 mefenpyrB-1203 2-3 mefenpyr B-1204 2-4 mefenpyr B-1205 2-5 mefenpyr B-1206 2-6mefenpyr B-1207 2-7 mefenpyr B-1208 2-8 mefenpyr B-1209 2-9 mefenpyrB-1210 2-1 H-11 B-1211 2-2 H-11 B-1212 2-3 H-11 B-1213 2-4 H-11 B-12142-5 H-11 B-1215 2-6 H-11 B-1216 2-7 H-11 B-1217 2-8 H-11 B-1218 2-9 H-11B-1219 2-1 H-12 B-1220 2-2 H-12 B-1221 2-3 H-12 B-1222 2-4 H-12 B-12232-5 H-12 B-1224 2-6 H-12 B-1225 2-7 H-12 B-1226 2-8 H-12 B-1227 2-9 H-12

The compounds I and the compositions according to the invention may alsohave a plant-strengthening action. Accordingly, they are suitable formobilizing the defense system of the plants against attack by unwantedmicroorganisms, such as harmful fungi, but also viruses and bacteria.Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances whichare capable of stimulating the defense system of treated plants in sucha way that, when subsequently inoculated by unwanted microorganisms, thetreated plants display a substantial degree of resistance to thesemicroorganisms.

The compounds I can be employed for protecting plants against attack byunwanted microorganisms within a certain period of time after thetreatment. The period of time within which their protection is effectedgenerally extends from 1 to 28 days, preferably from 1 to 14 days, afterthe treatment of the plants with the compounds I, or, after treatment ofthe seed, for up to 9 months after sowing.

The compounds I and the compositions according to the invention are alsosuitable for increasing the harvest yield.

Moreover, they have reduced toxicity and are tolerated well by theplants.

Hereinbelow, the preparation of pyridine compounds of the formula I isillustrated by way of examples, without limiting the subject matter ofthe present invention to the examples shown.

SYNTHESIS EXAMPLES

With appropriate modification of the starting materials, the proceduresgiven in the synthesis examples below were used to obtain furthercompounds I. The compounds obtained in this manner are listed in thetable that follows, together with physical data.

I. PREPARATION EXAMPLES Example 1 Preparation of4-hydroxy-3-(3-trifluoromethoxyphenyl)pyrano[3,2-b]pyridin-2-one [I-27]

Step 1: Pentafluorophenyl 3-hydroxypyridine-2-carboxylate

At 20-25° C. 13 g of N,N′-diisopropylcarbodiimide (DIC) were addeddropwise to a solution of 14 g of 3-hydroxypyridine-2-carboxylic acidand 18.5 g of pentafluorophenol in 700 ml of CH₂Cl₂. After the reactionhad ended (about 40 min), the solution was allowed to stand at 20-25° C.for about 12 hours. The solvent was removed, and the residue formed wasthen taken up in water and the solution was extracted with CH₂Cl₂. Theorganic phase gave, after drying and removal of the solvent, 29 g of thetitle compound.

Step 2: 4-Hydroxy-3-(3-trifluoromethoxyphenyl)pyrano[3,2-b]pyridin-2-one

3.5 g of K₂CO₃ were added to a solution of 0.64 g of pentafluorophenyl3-hydroxy-pyridine-2-carboxylate (from step 1) and 0.5 g of(3-trifluoromethoxyphenyl)acetyl chloride in 150 ml of acetonitrile, andthe mixture was stirred at 20-25° C. under an atmosphere of nitrogen forabout 12 hours. After filtration, the solvent was removed from thefiltrate and the residue obtained was taken up in water and, afteracidification to pH<4, extracted with CH₂Cl₂. The organic phase wasdried, then freed from the solvent. The residue gave, after preparativeHPLC [column: Luna (2), from Phenomenex, 300*50 mm 10 μm; mobile phase:water (+0.0375% trifluoroacetic acid) and acetonitrile in mixing ratiosof 80:20 and 50:50; flow rate 80 ml/min; detection at 220 and 254 nm),20-25° C.], 300 mg of the title compound.

¹H-NMR (CDCl₃) δ 8.55 (m, 1H), 7.74 (m, 1H), 7.58-7.73 (m, 3H),7.48-7.50 (m, 1H), 7.22-7.26 (m, 1H).

TABLE I Compounds of the formula I which correspond to the formula I.A:I.A

phys. data No. A E G M Y X R¹ R⁵ (R⁶)_(m) ¹H-NMR (δ [ppm])^(#)) I-1 N CHCH CH O O OH H 3-CF₃ (M): 8.57 (d), 7.96 (s), 7.78 (d), 7.75 (d),7.66-7.59 (m) I-2 N CH CH CH O O OH H 4-CF₃ (M): 8.57 (d), 7.82 (d),7.76-7.73 (m), 7.63 (d) I-3 N CH CH CH O O OH OCH₃ H (M): 8.52 (d), 7.72(d), 7.58-7.55 (m), 7.41-7.35 (m), 7.08-7.02 (m), 3.36 (s) I-4 N CH CHCH O O OH CN H (M): 8.47 (d), 7.69 (d), 7.59 (d), 7.53-7.50 (m), 7.34(t) I-5 N CH CH CH O O OH NO₂ H (D): 8.69 (d), 8.08 (d), 8.01 (d),7.83-7.78 (m), 7.67-7.62 (m) I-6 N CH CH CH O O OH F H (M): 8.50 (d),7.78 (d), 7.53 (m), 7.44 (m), 7.34-7.30 (m), 7.19- 7.09 (m) I-7 N CH CHCH O O OH H 3-F (D): 8.86 (d), 7.96 (d), 7.79-7.74 (m), 7.48-7.42 (m),7.36-7.30 (m), 7.16 (t) I-8 N CH CH CH O O OH Cl H (M): 8.18 (d), 7.84(s), 7.63-7.57 (m), 7.43-7.21 (m) I-9 N CH CH CH O O OH H 3-Cl (M): 8.16(m), 7.78 (m), 7.59 (m), 7.20-7.06 (m) I-10 N⁺ CH CH CH O O OH CHF₂ H(D): 8.65 (d), 7.96 (d), 7.78 (m), CF₃COO⁻ 7.68 (d), 7.58-7.52 (m), 7.34(d), 7.19-6.71 (m) I-11 N⁺ CH CH CH O O OH OCF₃ H (M): 8.66 (d), 7.97(d), 780-777 CF₃COO⁻ (m), 7.54-741 (m) I-12 N CH CH CH O O OH OCHF₂ H(D): 8.68 (d), 7.98 (d), 7.81-7.78 (m), 7.49-6.95 (m) I-13 N CH CH CH OO OH Br H (M): 8.44 (s), 7.78 (d), 7.67 (d), 7.49 (s), 7.37-7.33 (m),7.24- 7.20 (m) I-14 CH CH CH CH O O OH CF₃ H (M): 7.90 (t), 7.73 (t),7.66-7.61 (m), 7.46 (d), 7.40 (d), 7.33 (t) I-15 CH CH N CH O O OH CF₃ H(M): 8.59 (s), 8.39 (d), 7.91-7.90 (m), 7.72 (d), 7.61 (t), 7.45 (t),7.34 (d) I-16 CH CH CH N O O OH CF₃ H (M): 8.43-8.40 (m), 7.71 (d), 7.59(d), 7.44 (t), 7.37-7.34 (m) I-17 N CH CH CH S O OH CF₃ H (M): 8.63 (d),7.88 (d), 7.81 (d), 7.65 (t), 7.58-7.50 (m), 7.35 (d) I-18 N CH CH CH OO OH CF₃ H (M): 8.64 (s), 7.86 (d), 779 (d), 7.72-7.69 (m), 7.58 (t),7.43 (d) I-19 N—O¹⁾ CH CH CH O O OH CF₃ H (M): 8.39 (d), 7.80 (d),7.77-7.68 (m), 7.60 (t), 7.52 (t), 7.34 (d) I-20 N⁺ CH CH CH O O OH Cl4-Cl (D): 8.65 (d), 7.96 (d), 7.78-7.75 CF₃COO⁻ (m), 7.69 (s), 7.47 (d),7.41 (d) I-21 N C—Br CH CH O O OH CF₃ H (C): 7.81 (d), 7.36 (d),7.68-7.55 (m), 738 (d) I-22 N C— CH CH O O OH CF₃ H (C): 7.79 (d),7.69-7.65 (m), 7.59 OCH₂C₆H₅ (m), 7.46-7.26 (m), 7.12 (d), 5.42 (d) I-23N C—OH CH CH O O OH CF₃ H (M): 7.8 (d), 7.68-7.58 (m), 7.58 (m), 7.38(t), 6.92 (d) I-24 N—O¹⁾ CH CH CH O O OH CHF₂ H (C): 8.18 (d), 7.75-7.73(m), 7.58- 7.51 (m), 7.40-7.38 (m), 6.75 (t) I-25 N—O¹⁾ CH CH CH O O OHOCF₃ H (C): 8.18 (d), 7.54-7.53 (m), 7.48-7.44 (m), 7.39-7.36 (m) I-26N—O¹⁾ CH CH CH O O OH OCHF₂ H (C): 8.18 (d), 7.53-7.52 (m), 7.46-7.42(m), 7.34-7.26 (m), 6.50 (t) I-27 N CH CH CH O O OH H 3-OCF₃ (C): 8.55(m), 7.74 (m), 7.73- 7.58 (m), 7.50-7.48 (m), 7.26- 7.22 (m) I-28 N CHCH CH O O OH H 4-OCF₃ (C): 8.56 (d), 7.75-7.72 (m), 7.63-7.59 (m),7.32-7.30 (m) I-29 N CH CH CH O O OH H 3-OCH₃ (C): 8.54 (d), 7.71 (m),7.60 (m), 7.37 (m), 7.25 (m), 6.95 (m), 3.85 (s) I-30 N CH CH CH O O OHH 4-OCH₃ (C): 8.53 (d), 7.71 (m), 7.62 (m), 7.56 (m), 7.01 (m), 3.85 (s)I-31 N CH CH CH O O OH H 3-SCF₃ (C): 8.56 (d), 8.01 (s), 7.82 (m), 7.76(m), 7.67 (m), 7.60 (m), 7.51 (m) I-32 N CH CH CH S O OH OCF₃ H (C):8.64 (d), 7.88 (m), 7.54 (m), 7.46-7.39 (m), 7.39-7.36 (m) I-33 N CH CHCH S O OH CHF₂ H (C): 8.62 (d), 7.88 (m), 7.74 (m), 7.56-7.50 (m), 7.30(m), 6.60 (t) I-34 N CH CH CH O O OC(O)C(CH₃)₃ CF₃ H (C): 8.55 (d), 7.76(d), 7.69 (d), 7.61-7.48 (m), 7.31 (d), 1.06 (s) I-35 N CH CH CH O O OHCF₃ 5-CF₃ (C): 8.50-8.49 (m), 7.94 (d), 7.78 (d), 7.71 (d), 7.67 (s),7.54-7.50 (m) I-36 N CH CH CH O O OH CF₃ 4-CF₃ (C): 8.53-8.52 (m), 8.15(s), 7.85 (d), 7.68 (d), 7.56-7.53 (m), 7.38-7.36 (m) I-37 N CH CH CH OO OH CF₃ 4-F (M): 8.50-8.49 (m), 7.21 (d), 7.55-7.51 (m), 7.45 (d),7.36- 7.33 (m) I-38 N CH CH CH O O OH CF₃ 6-F (C): 8.55-8.53 (m), 7.69(d), 7.58-7.53 (m), 7.51-7.48 (m), 7.34-7.30 (m) I-39 N CH CH CH O O OHCF₃ — (C): 8.49-8.48 (m), 7.71 (d), 7.57-7.54 (m), 7.4 (s), 7.20 (s),2.18 (s) I-40 N CH CH CH O O OH Cl 6-F (M): 8.65-8.64 (m), 7.87 (d),7.73-7.70 (m), 7.43-7.35 (m), 7.19-7.17 (m) I-41 N CH CH CH O O OH Cl5-CF₃ (C): 8.58-8.57 (m), 7.79-7.77 (m), 7.69-7.60 (m) I-42 N CH CH CH OO OH I — (C): 8.56-8.55 (m), 7.98-7.96 (m), 7.77-7.75 (m), 7.63-7.60(m), 7.48-7.44 (m), 7.35-7.33 (m), 7.13-7.09 (m) I-43 N CH CH CH O O OHOCH₃ 4,5-F₂ (C): 8.54-8.53 (m), 7.74-7.71 (m), 7.61-7.58 (m), 7.21-7.18(m), 7.85-7.80 (m), 3.78 (s) I-44 N CH CH CH O O OH CF₃ 5-F (C):8.55-8.50 (m), 7.81-7.73 (m), 7.64-7.61 (m), 7.24-7.12 (m), 7.12-7.10(m) I-45 N CH CH CH O O OH CF₃ 5-Cl (C): 8.55-8.54 (m), 7.75-7.71 (m),7.74-7.61 (m), 7.51 (d), 7.24 (s) I-46 N CH CH CH O O OC(O)CH₃ CF₃ —(C): 8.54-8.53 (m), 7.74-7.72 (m), 7.66-7.64 (m), 7.58-7.28 (m),7.28-7.27 (m), 2.14 (s) I-47 N CH CH CH O O OH Cl 3,6-F₂ (C): 8.52-8.50(m), 7.72-7.70 (m), 7.60-7.57 (m), 7.17-7.13 (m), 7.05-7.00 (m) I-48 NCH CH CH O O OH CF₃ 3-F (C): 8.57-8.56 (m), 7.76 (d), 7.65-7.59 (m),7.28-7.26 (m), 3.87 (d) I-49 N CH CH CH O O OH OCF₃ — (C): 8.56 (d),7.76 (d), 7.64-7.61 (m), 7.56-7.51 (m), 7.41-7.38 (m) I-50 N CH CH CH OO OH Br 4-CF₃ (C): 8.59-8.58 (m), 7.98 (s), 7.80-7.77 (m), 7.69-7.65(m), 7.54-7.52 (m) I-51 N CH CH CH O O OH Cl 5-F (C): 8.51-8.50 (m),7.71-7.70 (m), 7.68-7.55 (m), 7.43-7.39 (m), 7.10-7.00 (m) I-52 N CH CHCH O O OH Cl 4,5-F₂ (C): 8.87-8.57 (m), 7.78-7.75 (m), 7.66-7.63 (m),7.39-7.34 (m), 7.28-7.24 (m) I-53 N CH CH CH O O OH Cl 4-OCF₃, (C):8.51-8.50 (m), 7.72-7.70 6-Cl (m), 7.60-7.57 (m), 7.27 (s) I-54 N CH CHCH O O OH Cl 4-CF₃, (C): 8.60-8.59 (m), 7.80-7.78 6-Cl (m), 7.71 (s),7.69-7.65 (m) I-55 N CH CH CH O O OH CF₃ 6-Br (M): 8.66-8.65 (m),8.00-7.98 (m), 7.90-7.87 (m), 7.82-7.80 (m), 7.74-7.71 (m), 7.52-7.48(m) I-56 N CH CH CH O O O—SO₂CH₃ CF₃ H (C): 8.67 (d), 7.83 (d),7.79-7.77 (m), 7.74-7.71 (m), 7.65-7.60 (m), 7.50 (d), 3.48 (s) ¹⁾N—O =N-oxide ^(#))Specification of the solvent: (C) = CDCl₃; (M) = CH₃OD; (D)= DMSO-d₆

Use Examples

The herbicidal activity of the compounds of the formula I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causeduniform germination of the test plants, unless this has been impaired bythe active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and then treatedwith the active compounds which had been suspended or emulsified inwater. For this purpose, the test plants were either sown directly andgrown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialmoieties, and 0 means no damage, or normal course of growth. A goodherbicidal activity is given at values of at least 70 and a very goodherbicidal activity is given at values of at least 85.

The plants used in the greenhouse experiments belonged to the followingspecies:

Bayer code Scientific name Common name ABUTH Abutilon theophrasti Chinajute ALOMY Alopecurus Blackgrass myosuroides AMARE Amaranthusretroflexus Carelessweed AVEFA Avena fatua spring wild-oat CHEALChenopodium album Pigweed GALAP Galium aparine Goosegrass SETFA Setariafaberi giant foxtail SETVI Setaria viridis Green foxtail

1) At an application rate of 0.5 kg/ha, the active compound I-35,applied by the pre-emergence method, showed very good herbicidalactivity against AMARE.

2) At application rates of 3.0 kg/ha and 2.0 kg/ha, the active compoundsI-10, I-11, I-13, I-20, I-22, I-26 and I-35 and the active compoundI-20, respectively, applied by the post-emergence method, showed verygood herbicide activity against ABUTH, and the active compound I-23,applied at an application rate of 3.0 kg/ha, showed good herbicidalactivity.

3) At an application rate of 3.0 kg/ha, the active compounds I-46, I-54and I-55, applied by the post-emergence method, showed very goodherbicidal activity against ALOMY.

4) At application rates of 0.5 kg/ha and 1.0 kg/ha, the active compoundsI-36, I-37, I-39, I-40, I-41, I-43, I-44, I-45, I-47, I-48, I-49, I-51and I-52 and the active compound I-42, respectively, applied by thepost-emergence method, showed very good herbicidal activity againstAMARE.

5) At an application rate of 3.0 kg/ha, the active compounds I-17, I-18,I-19, I-21, I-46, I-53 and I-55, applied by the post-emergence method,showed very good herbicidal activity against AVEFA.

6) At application rates of 3.0 kg/ha and 2.0 kg/ha, the active compoundsI-10, I-11, I-12, I-13, I-17, I-19, I-20, I-21, I-26 and I-27 and theactive compound I-20, respectively, applied by the post-emergencemethod, showed very good herbicidal activity against SETFA, and theactive compounds I-22 and I-23 showed good herbicidal activity at 3.0kg/ha.

7) At application rates of 0.5 kg/ha and 1.0 kg/ha, the active compoundsI-34, I-35, I-36, I-37, I-38, I-39, I-40, I-41, I-47, I-48, I-49, I-51and I-52 and the active compound I-50, respectively, applied by thepost-emergence method, showed very good herbicidal activity againstCHEAL.

8) At an application rate of 0.5 kg/ha, the active compounds I-35, I-37,I-38, I-44, I-45, I-48 and I-49, applied by the post-emergence method,showed very good herbicidal activity against ECHCG.

9) At an application rate of 0.5 kg/ha, the active compounds I-34 andI-38, applied by the post-emergence method, showed very good herbicidalactivity against GALAP.

10) At application rates of 0.5 kg/ha and 1.0 kg/ha, the activecompounds I-40, I-44, I-45 and I-51 and the active compound I-50,respectively, applied by the post-emergence method, showed very goodherbicidal activity against SETVI

1. A compound of the formula I

wherein: R¹ is O—R^(A), S(O)_(n)—R^(A) or O—S(O)_(n)—R^(A); R^(A) ishydrogen, C₁-C₄-alkyl, Z—C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,C₂-C₆-alkenyl, Z—C₃-C₆-cycloalkenyl, C₂-C₆-alkynyl,Z-(tri-C₁-C₄-alkyl)silyl, Z—C(═O)—R^(a), Z—NR^(i)—C(O)—NR^(i)R^(ii),Z—P(═O)(R^(a))₂, NR^(i)R^(ii), a 3- to 7-membered monocyclic or 9- or10-membered bicyclic saturated, unsaturated or aromatic heterocyclewhich contains 1, 2, 3 or 4 heteroatoms selected from the groupconsisting of O, N and S, which may be partially or fully substituted bygroups R^(a) and/or R^(b) and which is attached via carbon or nitrogen,R^(a) is hydrogen, OH, C₁-C₈-alkyl, C₁-C₄-haloalkyl, Z—C₃-C₆-cycloalkyl,C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl, C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy,Z—C₁-C₄-haloalkoxy, Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy,NR^(i)R^(ii), C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl,Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or 9- or10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatomsselected from the group consisting of O, N and S, where the cyclicgroups are unsubstituted or substituted by 1, 2, 3 or 4 groups R^(b);R^(i), R^(ii) independently of one another are hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl,Z—C₁-C₈-alkoxy, Z—C₁-C₈-haloalkoxy, Z—C(═O)—R^(a), Z-phenyl, a 3- to7-membered monocyclic or 9- or 10-membered bicyclic saturated,unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S and whichis attached via Z; or R^(i) and R^(ii) together with the nitrogen atomto which they are attached may also form a 5- or 6-membered monocyclicor 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S; Z is acovalent bond or C₁-C₄-alkylene; n is 0, 1 or 2; R² is phenylsubstituted by 1, 2, 3 or 4 groups R^(b); R^(b) independently of oneanother are Z—CN, Z—OH, Z—NO₂, Z-halogen, C₁C₈-alkyl, C₁-C₄-haloalkyl,C₂-C₈-alkenyl, C₂-C₈-alkynyl, Z—C₁-C₈-alkoxy, Z—C₁-C₈-halo-alkoxy,Z—C₃-C₁₀-cycloalkyl, O—Z—C₃-C₁₀-cycloalkyl, Z—C(═O)—R^(a), NR^(i)R^(ii),Z—(tri-C₁-C₄-alkyl)silyl, Z-phenyl and S(O)_(n)R^(bb), where R^(bb) isC₁-C₈-alkyl or C₁-C₆-haloalkyl; n is 0, 1 or 2; or R^(b) together with asecond group R^(b) attached to the adjacent carbon atom may form a five-or six-membered saturated or partially or fully unsaturated ring which,in addition to carbon atoms, may contain 1, 2 or 3 heteroatoms selectedfrom the group consisting of O, N and S; X is O; Y is O; E, G, M areC—R^(c), A is N; R^(c) is hydrogen or one of the groups mentioned forR^(b); where in the groups R^(A), and their subsubtituents, the carbonchains and/or the cyclic groups may be partially or fully substituted bygroups R^(b), or a N-oxide or an agriculturally suitable salt thereof.2. The compound of the formula I according to claim 1 in which R¹O—R^(A) or S(O)_(n)—R^(A); and R^(A) is hydrogen, C₁-C₄-alkyl,Z—C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl,Z—C₃-C₆-cycloalkenyl, C₂-C₆-alkynyl, Z-(tri-C₁-C₄-alkyl)silyl,Z—C(═O)—R^(a), Z—P(═O)(R^(a))₂, a 3- to 7-membered monocyclic or 9- or10-membered bicyclic saturated, unsaturated or aromatic heterocyclewhich contains 1, 2, 3 or 4 heteroatoms selected from the groupconsisting of O, N and S which may be partially or fully substituted bygroups R^(a) and/or R^(b) and which is attached via C or N, R^(a) ishydrogen, OH, C₁-C₄-alkyl, C₁-C₄-haloalkyl, Z—C₃-C₆-cycloalkyl,C₂-C₈-alkenyl, Z—C₅-C₆-cycloalkenyl, C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy,Z—C₁-C₄-haloalkoxy, Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy,NR^(i)R^(ii), C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl,Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or 9- or10-membered bicyclic heterocycle, comprising 1, 2, 3 or 4 heteroatomsselected from the group consisting of O, N and S, where the cyclicgroups are unsubstituted or substituted by 1, 2, 3 or 4 groups R^(b);R^(i), R^(ii) independently of one another are hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl,Z—C₁-C₈-alkoxy, or Z—C₁-C₈-haloalkoxy; or R^(i) and R^(ii) together withthe nitrogen atom to which they are attached may form a 5- or 6-memberedmonocyclic or 9- or 10-membered bicyclic heterocycle which contains 1,2, 3 or 4 heteroatoms selected from the group consisting of O, N and S.3. The compound of the formula I according to claim 1 in which R^(A) ishydrogen or C₁-C₆-alkylcarbonyl.
 4. The compound of the formula Iaccording to claim 1 in which R^(c) is hydrogen.
 5. The compound of theformula I according to claim 1 which corresponds to the formula

in which R⁵ and R⁶ are groups R^(b), R^(c) is H, and n is zero or aninteger from one to four.
 6. The compound of claim 5 and in which R¹ isOH, OCH₃, OC(O)CH₃, OC(O)CH₂CH₃, OC(O)CH(CH₃)₂, OC(O)C(CH₃)₃,OC(O)-c-C₃H₅, OC(O)—C₆H₅, OC(O)—CH₂C₆H₅, OC(O)CH₂Cl, OC(O)—CF₃,OC(O)—CH₂OCH₃, OC(O)—N(CH₃)₂ or OC(O)—OCH₂CH₃; and R² is phenylsubstituted by a group selected from the group consisting of 2-Br, 2-Cl,2,4-Cl₂, 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF₃, 2-Cl-5-CF₃,2-Cl-6-CF₃, 2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂, 2,6-F₂, 2-F-4-CF₃,2-F-5-CF₃, 2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F, 2-NO₂-5-F, 2-NO₂-6-F,2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃, 2-NO₂-3,6-F₂, 2-CN, 2-CH₃,2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃, 2-CH₃-5-CF₃, 2-CH₃-6-CF₃,2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F, 2-OCH₃-6-F, 2-OCH₃-4-CF₃,2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂, 2-CHF₂, 2-CHF₂-4-F,2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF₂-4-CF₃, 2-CHF₂-5-CF₃, 2-CHF₂-6-CF₃,2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F, 2-CF₃-4-CF₃,2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂, 2-OCHF₂-4-F,2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃, 2-OCHF₂-6-CF₃,2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F, 2-OCF₃-6-F,2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃ and 2-OCF₃-3,6-F₂.
 7. Acomposition comprising a herbicidally effective amount of at least onepyridine compound of the formula I or an agriculturally suitable saltthereof according to claim 1 and auxiliaries customary for formulatingcrop protection agents.
 8. The composition according to claim 7 whichcomprises at least one further active compound.
 9. The compositionaccording to claim 7 which comprises two further active compounds fromthe group of the herbicides and/or safeners.
 10. A method forcontrolling unwanted vegetation which comprises allowing a herbicidallyeffective amount of at least one compound of claim 1 to act on plants,their seed and/or their habitat.
 11. The method of claim 10, wherein R¹O—R^(A) or S(O)_(n)—R^(A); and R^(A) is hydrogen, C₁-C₄-alkyl,Z—C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, Z—C₃-C₆-cycloalkenyl, C₂-C₆-alkynyl,Z-(tri-C₁-C₄-alkyl)silyl, Z—C(═O)—R^(a), Z—P(═O)(R^(a))₂, a 3- to7-membered monocyclic or 9- or 10-membered bicyclic saturated,unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S which maybe partially or fully substituted by groups R^(a) and/or R^(b) and whichis attached via C or N, R^(a) is hydrogen, OH, C₁-C₈-alkyl,C₁-C₄-haloalkyl, Z—C₃-C₆-cycloalkyl, C₂-C₈-alkenyl,Z—C₅-C₆-cycloalkenyl, C₂-C₈-alkynyl, Z—C₁-C₆-alkoxy, Z—C₁-C₄-haloalkoxy,Z—C₃-C₈-alkenyloxy, Z—C₃-C₈-alkynyloxy, NR^(i)R^(ii),C₁-C₆-alkylsulfonyl, Z-(tri-C₁-C₄-alkyl)silyl, Z-phenyl, Z-phenoxy,Z-phenylamino or a 5- or 6-membered monocyclic or 9-, or 10-memberedbicyclic heterocycle, comprising 1, 2, 3 or 4 heteroatoms selected fromthe group consisting of O, N and S, where the cyclic groups areunsubstituted or substituted by 1, 2, 3 or 4 groups R^(b); R^(i), R^(ii)independently of one another are hydrogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl,C₃-C₈-alkenyl, C₃-C₈-alkynyl, Z—C₃-C₆-cycloalkyl, Z—C₁-C₈-alkoxy, orZ—C₁-C₈-haloalkoxy; or R^(i) and R^(ii) together with the nitrogen atomto which they are attached may form a 5- or 6-membered monocyclic or 9-or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S.
 12. Themethod of claim 10, wherein R^(A) is hydrogen or C₁-C₆-alkylcarbonyl.13. The method of claim 10, wherein R^(c) is hydrogen.
 14. The method ofclaim 10, wherein the compound corresponds to the formula

in which R⁵ and R⁶ are groups R^(b) and n is zero or an integer from oneto four.
 15. The method of claim 10, wherein R¹ is OH, OCH₃, OC(O)CH₃,OC(O)CH₂CH₃, OC(O)CH(CH₃)₂, OC(O)C(CH₃)₃, OC(O)-c-C₃H₅, OC(O)—C₆H₅,OC(O)—CH₂C₆H₅, OC(O)CH₂Cl, OC(O)—CF₃, OC(O)—CH₂OCH₃, OC(O)—N(CH₃)₂ orOC(O)—OCH₂CH₃; R² is phenyl substituted by a group selected from thegroup consisting of 2-Br, 2-Cl, 2,4-Cl₂, 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F,2-Cl-4-CF₃, 2-Cl-5-CF₃, 2-Cl-6-CF₃, 2-Cl-3,6-F₂, 2-F, 2,4-F₂, 2,5-F₂,2,6-F₂, 2-F-4-CF₃, 2-F-5-CF₃, 2-F-6-CF₃, 2,3,6-F₃, 2-NO₂, 2-NO₂-4-F,2-NO₂-5-F, 2-NO₂-6-F, 2-NO₂-4-CF₃, 2-NO₂-5-CF₃, 2-NO₂-6-CF₃,2-NO₂-3,6-F₂, 2-CN, 2-CH₃, 2-CH₃-4-F, 2-CH₃-5-F, 2-CH₃-6-F, 2-CH₃-4-CF₃,2-CH₃-5-CF₃, 2-CH₃-6-CF₃, 2-CH₃-3,6-F₂, 2-OCH₃, 2-OCH₃-4-F, 2-OCH₃-5-F,2-OCH₃-6-F, 2-OCH₃-4-CF₃, 2-OCH₃-5-CF₃, 2-OCH₃-6-CF₃, 2-OCH₃-3,6-F₂,2-CHF₂, 2-CHF₂-4-F, 2-CHF₂-5-F, 2-CHF₂-6-F, 2-CHF₂-4-CF₃, 2-CHF₂-5-CF₃,2-CHF₂-6-CF₃, 2-CHF₂-3,6-F₂, 2-CF₃, 2-CF₃-4-F, 2-CF₃-5-F, 2-CF₃-6-F,2-CF₃-4-CF₃, 2-CF₃-5-CF₃, 2-CF₃-6-CF₃, 2-CF₃-3,6-F₂, 2-OCHF₂,2-OCHF₂-4-F, 2-OCHF₂-5-F, 2-OCHF₂-6-F, 2-OCHF₂-4-CF₃, 2-OCHF₂-5-CF₃,2-OCHF₂-6-CF₃, 2-OCHF₂-3,6-F₂, 2-OCF₃, 2-OCF₃-4-F, 2-OCF₃-5-F,2-OCF₃-6-F, 2-OCF₃-4-CF₃, 2-OCF₃-5-CF₃, 2-OCF₃-6-CF₃ and 2-OCF₃-3,6-F₂.